((Title))
Synthesis of Arylamines via Aminium Radicals -819158835390[a]Thomas D. Svejstrup, Dr. Alessandro Ruffoni, Dr. Fabio Juliá, Valentin M. Aubert and Dr. Daniele LeonoriSchool of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UKE-mail: daniele.leonori@manchester.ac.ukWebsite: information for this article is given via a link at the end of the document.00[a]Thomas D. Svejstrup, Dr. Alessandro Ruffoni, Dr. Fabio Juliá, Valentin M. Aubert and Dr. Daniele LeonoriSchool of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UKE-mail: daniele.leonori@manchester.ac.ukWebsite: information for this article is given via a link at the end of the document.Thomas D. Svejstrup,a Alessandro Ruffoni,a Fabio Juliá,a Valentin M. Auberta and Daniele Leonoria*Abstract: Arylamines constitute the core structure of many therapeutic agents, agrochemicals and organic materials. The development of methodologies for the efficient and selective construction of these structural motifs from simple building blocks is desirable but still challenging. Here, we demonstrate that protonated electron poor O-aryl hydroxylamines lead, in the presence of Ru(bpy)3Cl2, to the formation of aminium radicals. These highly electrophilic species undergo polarized radical addition to aromatics in high yield and selectivity. We have successfully applied this methodology to the late-stage modification of chiral catalyst templates, therapeutic agents and natural products.N,N-Dialkyl-aryl-amines are a privileged scaffold found in blockbuster drugs, agrochemicals and organic materials (Scheme 1A).PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5WaXRha3U8L0F1dGhvcj48WWVhcj4yMDE0PC9ZZWFyPjxS
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ADDIN EN.CITE.DATA [1] These molecular frameworks are usually assembled by Pd(0)- or Cu(I/II)-catalysed cross-couplings of amine nucleophiles and aryl-halides (i.e. Ullmann ADDIN EN.CITE <EndNote><Cite><Author>Sambiagio</Author><Year>2014</Year><RecNum>1658</RecNum><DisplayText><style face="superscript">[2]</style></DisplayText><record><rec-number>1658</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496650213">1658</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>C. Sambiagio</author><author>S. P. Marsden</author><author>A. J. Blacker</author><author>P. C. McGowan</author></authors></contributors><titles><secondary-title>Chem. Soc. Rev.</secondary-title></titles><periodical><full-title>Chem. Soc. Rev.</full-title></periodical><pages>3525</pages><volume>43</volume><dates><year>2014</year></dates><urls></urls></record></Cite></EndNote>[2] and Buchwald-HartwigPEVuZE5vdGU+PENpdGU+PEF1dGhvcj5HdXJhbTwvQXV0aG9yPjxZZWFyPjE5OTQ8L1llYXI+PFJl
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ADDIN EN.CITE.DATA [6]Nitrogen-radicals ADDIN EN.CITE <EndNote><Cite><Author>Zard</Author><Year>2008</Year><RecNum>1057</RecNum><DisplayText><style face="superscript">[7]</style></DisplayText><record><rec-number>1057</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1415292982">1057</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>S. Z. Zard</author></authors></contributors><titles><title>Recent progress in the generation and use of nitrogen-centred radicals</title><secondary-title>Chem. Soc. Rev.</secondary-title></titles><periodical><full-title>Chem. Soc. Rev.</full-title></periodical><pages>1603-1618</pages><volume>37</volume><dates><year>2008</year></dates><urls></urls></record></Cite></EndNote>[7] are highly reactive species that are now witnessing a resurgence of synthetic interest owing to the ability of photoredox catalysisPEVuZE5vdGU+PENpdGU+PEF1dGhvcj5QcmllcjwvQXV0aG9yPjxZZWFyPjIwMTM8L1llYXI+PFJl
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ADDIN EN.CITE.DATA [8] to promote single-electron transfer (SET) ADDIN EN.CITE <EndNote><Cite><Author>Studer</Author><Year>2015</Year><RecNum>1430</RecNum><DisplayText><style face="superscript">[9]</style></DisplayText><record><rec-number>1430</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1462470692">1430</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>A. Studer</author><author>D. P. Curran</author></authors></contributors><titles><title>Catalysis of Radical Reactions: A Radical Chemistry Perspective</title><secondary-title>Angew. Chem. Int. Ed.</secondary-title></titles><periodical><full-title>Angew. Chem. Int. Ed.</full-title></periodical><pages>58-102</pages><volume>55</volume><dates><year>2015</year></dates><urls></urls></record></Cite></EndNote>[9] processes under mild conditions.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5DaGVuPC9BdXRob3I+PFllYXI+MjAxNjwvWWVhcj48UmVj
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ADDIN EN.CITE.DATA [11] and sulfamidyl radicals ADDIN EN.CITE <EndNote><Cite><Author>Qin</Author><Year>2014</Year><RecNum>1080</RecNum><DisplayText><style face="superscript">[12]</style></DisplayText><record><rec-number>1080</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1423769179">1080</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Q. Qin</author><author>S. Yu</author></authors></contributors><titles><secondary-title>Org. Lett.</secondary-title></titles><periodical><full-title>Org. Lett.</full-title></periodical><pages>3504</pages><volume>16</volume><dates><year>2014</year></dates><urls></urls></record></Cite><Cite><Author>Meyer</Author><Year>2016</Year><RecNum>1693</RecNum><record><rec-number>1693</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1498637991">1693</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>A. U. Meyer</author><author>A. L. Berger</author><author>B. Konig</author></authors></contributors><titles><secondary-title>Chem. Commun.</secondary-title></titles><periodical><full-title>Chem. Commun.</full-title></periodical><pages>10918</pages><volume>52</volume><dates><year>2016</year></dates><urls></urls></record></Cite><Cite><Author>Ito</Author><Year>2017</Year><RecNum>1732</RecNum><record><rec-number>1732</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1501745569">1732</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>E. Ito</author><author>T. Fukushima</author><author>T. Kawakami</author><author>K. Murakami</author><author>K. Itami</author></authors></contributors><titles><secondary-title>Chem</secondary-title></titles><periodical><full-title>Chem</full-title></periodical><pages>383</pages><volume>2</volume><dates><year>2017</year></dates><urls></urls></record></Cite></EndNote>[12] have been successfully coupled with highly electron rich aromatics (e.g. indole, pyrrole), the use of di-alkyl-substituted nitrogen radicals – aminyl radicals – in related arylations has yet to be described. This lack of synthetic application can be explained by the intrinsic nucleophilic nature of aminyls that causes repulsive interactions between their lone pair and the aromatic.PEVuZE5vdGU+PENpdGU+PEF1dGhvcj5NaWNoaWVqZGE8L0F1dGhvcj48WWVhcj4xOTcwPC9ZZWFy
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ADDIN EN.CITE.DATA [10d, 10i, 14] that are isoelectronic to alkyl-radicals but carry a formal positive charge (Scheme 1B). This makes them powerful electrophiles that undergo highly polarized radical processes. Indeed, pioneering work from Minisci showed that N–Cl-amines can be arylated upon photochemical N–Cl bond homolysis. ADDIN EN.CITE <EndNote><Cite><Author>Minisci</Author><Year>1965</Year><RecNum>1666</RecNum><DisplayText><style face="superscript">[15]</style></DisplayText><record><rec-number>1666</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496656651">1666</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>F. Minisci</author><author>R. Galli</author></authors></contributors><titles><secondary-title>Tetrahedron Lett.</secondary-title></titles><periodical><full-title>Tetrahedron Lett.</full-title></periodical><pages>433</pages><volume>8</volume><dates><year>1965</year></dates><urls></urls></record></Cite><Cite><Author>Bock</Author><Year>1965</Year><RecNum>1667</RecNum><record><rec-number>1667</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496657158">1667</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>H. Bock</author><author>K.-L. Kompa</author></authors></contributors><titles><secondary-title>Angew. Chem. Int. Ed.</secondary-title></titles><periodical><full-title>Angew. Chem. Int. Ed.</full-title></periodical><pages>783</pages><volume>4</volume><dates><year>1965</year></dates><urls></urls></record></Cite><Cite><Author>Minisci</Author><Year>1973</Year><RecNum>1665</RecNum><record><rec-number>1665</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496656393">1665</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>F. Minisci</author></authors></contributors><titles><secondary-title>Synthesis</secondary-title></titles><periodical><full-title>Synthesis</full-title></periodical><pages>1</pages><dates><year>1973</year></dates><urls></urls></record></Cite></EndNote>[15] While successful, these reactions have not been employed in mainstream organic synthesis owing to three main limitations: (i) the aromatic is a co-solvent (10-20 equiv.); (ii) high-energy light ( < 280 nm) is required and (iii) the reactions are run in refluxing AcOH–H2SO4. ADDIN EN.CITE <EndNote><Cite><Author>Minisci</Author><Year>1973</Year><RecNum>1665</RecNum><DisplayText><style face="superscript">[15c]</style></DisplayText><record><rec-number>1665</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496656393">1665</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>F. Minisci</author></authors></contributors><titles><secondary-title>Synthesis</secondary-title></titles><periodical><full-title>Synthesis</full-title></periodical><pages>1</pages><dates><year>1973</year></dates><urls></urls></record></Cite></EndNote>[15c] We have recently developed a visible-light-mediated synthesis of iminyl ADDIN EN.CITE <EndNote><Cite><Author>Davies</Author><Year>2015</Year><RecNum>1270</RecNum><DisplayText><style face="superscript">[16]</style></DisplayText><record><rec-number>1270</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1442160880">1270</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>J. Davies</author><author>S. G. Booth</author><author>S. Essafi</author><author>R. W. A. Dryfe</author><author>D. Leonori</author></authors></contributors><titles><title>Visible Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination- and Iminohydroxylation-Cyclization Reactions?? ??</title><secondary-title>Angew. Chem. Int. Ed.</secondary-title></titles><periodical><full-title>Angew. Chem. Int. Ed.</full-title></periodical><pages>14017</pages><volume>54</volume><dates><year>2015</year></dates><urls></urls></record></Cite></EndNote>[16] and amidyl ADDIN EN.CITE <EndNote><Cite><Author>J. Davies</Author><Year>2016</Year><RecNum>1511</RecNum><DisplayText><style face="superscript">[11c]</style></DisplayText><record><rec-number>1511</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1471838868">1511</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>J. Davies,</author><author>T. D. Svejstrup</author><author>D. Fernandez Reina</author><author>N. S. Sheikh</author><author>D. Leonori</author></authors></contributors><titles><title>Visible-Light-Mediated Synthesis of Amidyl Radicals: Transition Metal-Free Hydroamination and N-Arylation Reactions</title><secondary-title>J. Am. Chem. Soc.</secondary-title></titles><periodical><full-title>J. Am. Chem. Soc.</full-title></periodical><pages>8092</pages><volume>138</volume><dates><year>2016</year></dates><urls></urls></record></Cite></EndNote>[11c] radicals via reductive SET fragmentation of electron poor O-aryl oximes and aryloxyamides. We envisaged that such approach might have enabled access to aminium radicals for direct aromatic amination. In this paper we describe our work in the area that has resulted in a powerful method for the fast construction of aryl amines (Scheme 1C).Scheme 1. Aryl amines and aminium radicals. At the outset we hypothesized a strategy relying on our reductive SET approach for nitrogen-radical generation in the presence of a Br?nsted acid (Scheme 2A). Depending on the acid’s pKa two mechanistic pathways are possible. In the case of a weak acid, SET reduction and fragmentation of electron poor O-aryl-hydroxylamine A would generate the aminyl radical B that upon protonation would lead to the key aminium radical C ready for intermolecular arylation (Path a). As aminyl and aminium radicals are short-lived (0 ≈ 1–10 s) ADDIN EN.CITE <EndNote><Cite><Author>Wagner</Author><Year>1996</Year><RecNum>1659</RecNum><DisplayText><style face="superscript">[17]</style></DisplayText><record><rec-number>1659</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496655770">1659</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>B. D. Wagner</author><author>G. Ruel</author><author>J. Lusztyk</author></authors></contributors><titles><secondary-title>J. Am. Chem. Soc.</secondary-title></titles><periodical><full-title>J. Am. Chem. Soc.</full-title></periodical><pages>13</pages><volume>118</volume><dates><year>1996</year></dates><urls></urls></record></Cite></EndNote>[17] and undergo fast H-atom abstraction, ADDIN EN.CITE <EndNote><Cite><Author>Lockhart</Author><Year>1976</Year><RecNum>1670</RecNum><DisplayText><style face="superscript">[18]</style></DisplayText><record><rec-number>1670</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496657462">1670</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>R. W. Lockhart</author><author>R. W. Snyder</author><author>Y. L. Chow</author></authors></contributors><titles><secondary-title>J. Chem. Soc. Chem. Commun.</secondary-title></titles><periodical><full-title>J. Chem. Soc. Chem. Commun.</full-title></periodical><pages>52</pages><dates><year>1976</year></dates><urls></urls></record></Cite><Cite><Author>Xu</Author><Year>2015</Year><RecNum>1660</RecNum><record><rec-number>1660</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496655879">1660</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>P. Xu</author><author>G. Wang</author><author>Y. Zhu</author><author>W. Li</author><author>Y. Cheng</author><author>S. Li</author><author>C. Zhu</author></authors></contributors><titles><secondary-title>Angew. Chem. Int. Ed.</secondary-title></titles><periodical><full-title>Angew. Chem. Int. Ed.</full-title></periodical><pages>2992</pages><volume>128</volume><dates><year>2015</year></dates><urls></urls></record></Cite></EndNote>[18] a better approach would rely in the use of a strong acid able to protonate A leading to the ammonium salt E (Path b). This initial protonation intrinsically leads to many advantages as: (i) SET reduction of E is expected to be more facile, ADDIN EN.CITE <EndNote><Cite><Author>Fukuzumi</Author><Year>1986</Year><RecNum>1698</RecNum><DisplayText><style face="superscript">[19]</style></DisplayText><record><rec-number>1698</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1499430241">1698</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>S. Fukuzumi</author><author>K. Ishikawa</author><author>K. Hironaka</author><author>T. Tanaka</author></authors></contributors><titles><secondary-title>J. Chem. Soc., Perkin Trans. 2</secondary-title></titles><periodical><full-title>J. Chem. Soc., Perkin Trans. 2</full-title></periodical><pages>751</pages><dates><year>1986</year></dates><urls></urls></record></Cite></EndNote>[19] (ii) the formation of aminyl B is by-passed, (iii) the 0 of C will be enhanced ADDIN EN.CITE <EndNote><Cite><Author>Chow</Author><Year>1978</Year><RecNum>1661</RecNum><DisplayText><style face="superscript">[13c]</style></DisplayText><record><rec-number>1661</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496655997">1661</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Y. L. Chow</author><author>W. C. Danen</author><author>S. F. Nelsen</author><author>D. H. Rosenblatt</author></authors></contributors><titles><secondary-title>Chem. Rev.</secondary-title></titles><periodical><full-title>Chem. Rev.</full-title></periodical><pages>243</pages><volume>78</volume><dates><year>1978</year></dates><urls></urls></record></Cite></EndNote>[13c] and (iv) the strong acid will maintain the N-atom protonated during the entire reaction sequence synergistically insulating the arylamine D from SET oxidation (decomposition) and/or further amination (over reactivity). Furthermore, as E is expected to be the strongest electrophore in the system, any potential SET oxidation of the aromatic partner ADDIN EN.CITE <EndNote><Cite><Author>Romero</Author><Year>2015</Year><RecNum>1434</RecNum><DisplayText><style face="superscript">[20]</style></DisplayText><record><rec-number>1434</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1462472590">1434</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>N. A. Romero</author><author>K. A. Margrey</author><author>N. E. Tay</author><author>D. A. Nicewicz</author></authors></contributors><titles><title>Site-selective arene C-H amination via photoredox catalysis</title><secondary-title>Science</secondary-title></titles><periodical><full-title>Science</full-title></periodical><pages>1326</pages><volume>349</volume><dates><year>2015</year></dates><urls></urls></record></Cite><Cite><Author>Niu</Author><Year>2017</Year><RecNum>1730</RecNum><record><rec-number>1730</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1501745412">1730</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>L. Niu</author><author>Hong Yi</author><author>S. Wang</author><author>T. Liu</author><author>J. Liu</author><author>A. Lei</author></authors></contributors><titles><secondary-title>Nat. Com.</secondary-title></titles><periodical><full-title>Nat. Com.</full-title></periodical><pages>1</pages><volume>8</volume><dates><year>2017</year></dates><urls></urls></record></Cite></EndNote>[20] will be minimised. Overall, this approach would represent an umpolung alternative to the photoredox amination protocols developed by Nicewicz[20a] and Lei[20b] where nucleophilic pyrazoles react with aromatic radical cations.This strategy was evaluated using piperidine 1a (Ered = –0.9 V vs SCE in CH3CN) prepared in one step from commercial materials on multi-gram scale, ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] t-Bu-benzene 2, Ru(bpy)3Cl2 as the photoredox catalyst in CH3CN under blue LEDs irradiation (450 nm) (Scheme 2B). Without Br?nsted acid or in the presence of AcOH or TFA no product was obtained along with quantitative recovery of 1a and 2 (entries 1–3). To our delight, using pTsOH, 3a was formed in 19% yield (3:1 para:meta) (entry 4) and further evaluation revealed that HClO4 (70% in H2O) exhibited optimal conversion in just 15 min at room temperature (entry 5). Other aminium radical precursors with different aromatic substitution patterns have been evaluated but they provided 3a in very low yield (if any) leaving 1a as the optimum electrophore for this arylation strategy. ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] In line with our working hypothesis, (i) the acid could not be used in sub-stoichiometric amounts (entry 6) and (ii) 1H NMR studies revealed that only pTsOH and HClO4 led to protonation of 1a. ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] Control experiments confirmed the requirement for Ru(bpy)3Cl2 but blue LEDs irradiation was not necessary to observe product formation (entry 7). ADDIN EN.CITE <EndNote><Cite><Author>Quantum</Author><RecNum>1792</RecNum><DisplayText><style face="superscript">[22]</style></DisplayText><record><rec-number>1792</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1506687552">1792</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Quantum</author></authors></contributors><titles></titles><dates></dates><urls></urls></record></Cite></EndNote>[22] However, higher yields were consistently obtained when the reactions were run under continuous irradiation during the scope evaluation. ADDIN EN.CITE <EndNote><Cite><Author>Dibenzyl</Author><RecNum>1793</RecNum><DisplayText><style face="superscript">[23]</style></DisplayText><record><rec-number>1793</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1506690978">1793</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>Dibenzyl</author></authors></contributors><titles></titles><dates></dates><urls></urls></record></Cite></EndNote>[23] This suggests a complex interplay of photochemical and “dark” pathways cooperating for the formation of the reaction product. For example, 1a–H+ could undergo SET reduction from the visible-light-excited *Ru(II) to generate the highly electrophilic piperidinium radical 4 (calculated electrophilicity index, rc+ = 13.0) ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] (Scheme 2C). Polarized radical amination would form the carbon-radical 5 that can deliver the protonated product 3–H+ by (i) closing the photoredox cycle or (ii) reacting in a propagative manner with 1a–H+. In order to evaluate the feasibility of the latter pathway, we have studied by DFT the key step in the propagation cycle (5 + 1a-H+ 4 + 3-H+) and found it exergonic (G? = –15.2 kcal mol–1). ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] The observed “dark” reactivity might arise from the ability of ground-state Ru(bpy)3Cl2 (E1/2ox = +1.29 V vs SCE in CH3CN) ADDIN EN.CITE <EndNote><Cite><Author>C. R. Bock</Author><Year>1979</Year><RecNum>1722</RecNum><DisplayText><style face="superscript">[24]</style></DisplayText><record><rec-number>1722</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1501582790">1722</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>C. R. Bock, J. A. Connor</author><author>A. R. Gutierrez</author><author>Thomas J. Meyer</author><author>D. G. Whitten</author><author>B. P. Sullivan</author><author>J. K. Nagle</author></authors></contributors><titles><secondary-title>J. Am. Chem. Soc.</secondary-title></titles><periodical><full-title>J. Am. Chem. Soc.</full-title></periodical><pages>4815</pages><volume>101</volume><dates><year>1979</year></dates><urls></urls></record></Cite></EndNote>[24] to promote the SET reduction of 1a–H+ and act as an electron-relay ADDIN EN.CITE <EndNote><Cite><Author>Boursalian</Author><Year>2013</Year><RecNum>1725</RecNum><DisplayText><style face="superscript">[25]</style></DisplayText><record><rec-number>1725</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1501744687">1725</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>G. B. Boursalian</author><author>M.-Y. Ngai</author><author>K. N. Hojczyk</author><author>T. Ritter</author></authors></contributors><titles><secondary-title>J. Am. Chem. Soc.</secondary-title></titles><periodical><full-title>J. Am. Chem. Soc.</full-title></periodical><pages>13278</pages><volume>135</volume><dates><year>2013</year></dates><urls></urls></record></Cite><Cite><Author>Foo</Author><Year>2014</Year><RecNum>1072</RecNum><record><rec-number>1072</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1415292982">1072</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>K. Foo</author><author>E. Sella</author><author>I. Thomé</author><author>M. D. Eastgate</author><author>P. S. Baran</author></authors></contributors><titles><secondary-title>J. Am. Chem. Soc.</secondary-title></titles><periodical><full-title>J. Am. Chem. Soc.</full-title></periodical><pages>5279</pages><volume>136</volume><dates><year>2014</year></dates><urls></urls></record></Cite><Cite><Author>Boursalian</Author><RecNum>1728</RecNum><record><rec-number>1728</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1501745181">1728</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>G. B. Boursalian</author><author>W. S. Ham</author><author>A. R. Mazzotti</author><author>T. Ritter</author></authors></contributors><titles></titles><dates><year>2016</year></dates><urls></urls></record></Cite></EndNote>[25] catalyst/radical chain initiator. ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] Indeed, we have been able to detected the formation of Ru(III) by UV/Vis spectroscopy in stoichiometric “dark” experiments. We believe that upon protonation, 1a–H+ becomes a powerful oxidant ADDIN EN.CITE <EndNote><Cite><Author>Fukuzumi</Author><Year>1986</Year><RecNum>1698</RecNum><DisplayText><style face="superscript">[19, 26]</style></DisplayText><record><rec-number>1698</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1499430241">1698</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>S. Fukuzumi</author><author>K. Ishikawa</author><author>K. Hironaka</author><author>T. Tanaka</author></authors></contributors><titles><secondary-title>J. Chem. Soc., Perkin Trans. 2</secondary-title></titles><periodical><full-title>J. Chem. Soc., Perkin Trans. 2</full-title></periodical><pages>751</pages><dates><year>1986</year></dates><urls></urls></record></Cite><Cite><Author>Fukuzumi</Author><Year>1989</Year><RecNum>1697</RecNum><record><rec-number>1697</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1499430172">1697</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>S. Fukuzumi</author><author>M. Chiba</author><author>T. Tanaka</author></authors></contributors><titles><secondary-title>Chem. Lett.</secondary-title></titles><periodical><full-title>Chem. Lett.</full-title></periodical><pages>31</pages><dates><year>1989</year></dates><urls></urls></record></Cite></EndNote>[19, 26] (calculated ADDIN EN.CITE <EndNote><Cite><Author>Roth</Author><Year>2016</Year><RecNum>1605</RecNum><DisplayText><style face="superscript">[27]</style></DisplayText><record><rec-number>1605</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1489585643">1605</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>H. G. Roth</author><author>N. A. Romero</author><author>D. A. Nicewicz</author></authors></contributors><titles><secondary-title>Synlett</secondary-title></titles><periodical><full-title>Synlett</full-title></periodical><pages>714</pages><volume>27</volume><dates><year>2016</year></dates><urls></urls></record></Cite></EndNote>[27] Ered(1a-H+) = +1.7 V vs SCE) and might be responsible for this unforeseen reactivity. ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21]With optimal conditions in hand, we examined the aromatic partner scope using piperidine 1a (Scheme 3). Pleasingly, the reaction displayed broad applicability and a series of differentially substituted benzene derivatives were successfully employed. The high electrophilicity of aminium radicals is advantageous as it enables reaction with weakly (3a–d) as well as strongly electron rich aromatics (3e–j). In the case of mono-substituted benzenes, reaction occurred preferentially at the para position underlining the importance of polar and steric effects in the radical amination step. This selectivity can be rationalised by computing the Fukui indices ADDIN EN.CITE <EndNote><Cite><Author>Cheng</Author><Year>2016</Year><RecNum>1672</RecNum><DisplayText><style face="superscript">[28]</style></DisplayText><record><rec-number>1672</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496657788">1672</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>J. Cheng</author><author>X. Deng</author><author>G. Wang</author><author>Y. Li</author><author>X. Cheng</author><author>G. Li</author></authors></contributors><titles><secondary-title>Org. Lett.</secondary-title></titles><periodical><full-title>Org. Lett.</full-title></periodical><pages>4538</pages><volume>18</volume><dates><year>2016</year></dates><urls></urls></record></Cite></EndNote>[28] for the aromatics. ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] Halogenated anisoles (3k,l), benzodioxolane (3m) and chromanone (3n) also underwent amination in useful yields. Polycyclic aromatics reacted very well and we expanded the chemistry to the selective amination of naphthalene (3o), 2-metoxy- (3p), 2-bromo- (3q), and 2-acetyl-naphatlene (3r) as well as 1-bromo- (3s), 1-chloro- (3t) and 1-cyano-naphtalene (3u). The successful implementation of halogen-containing aromatics (3l,q,s,t) offers orthogonal reactivity to the well-established Buchwald-Hartwig couplings. The reaction was also amenable to the installation of the piperidine ring onto fluorene (3v), fluorenone (3w), dibenzothiophene (3y), azulene (3x), 8-MeO-quinoline (3z) and PMP-pyrrole (3aa) and N-Me-indole (3ab).Scheme 2. Possible mechanistic pathways, reaction optimization and proposed mechanistic analysis.We were particularly keen in demonstrating the power of this strategy by engaging some of the most frequent nitrogen heterocycles found in small-molecule drugs. ADDIN EN.CITE <EndNote><Cite><Author>Vitaku</Author><Year>2014</Year><RecNum>1650</RecNum><DisplayText><style face="superscript">[1a, 1c]</style></DisplayText><record><rec-number>1650</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496645204">1650</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>E. Vitaku</author><author>D. T. Smith</author><author>J. T. Njardarson</author></authors></contributors><titles><secondary-title>J. Med. Chem.</secondary-title></titles><periodical><full-title>J. Med. Chem.</full-title></periodical><pages>10257-10274</pages><volume>57</volume><dates><year>2014</year></dates><urls></urls></record></Cite><Cite><Author>Welsch</Author><Year>2010</Year><RecNum>1092</RecNum><record><rec-number>1092</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1425559919">1092</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>M. E. Welsch</author><author>S. A. Snyder</author><author>B. R. Stockwell</author></authors></contributors><titles><secondary-title>Curr. Opin. Chem. Biol.</secondary-title></titles><periodical><full-title>Curr. Opin. Chem. Biol.</full-title></periodical><pages>347</pages><volume>14</volume><dates><year>2010</year></dates><urls></urls></record></Cite></EndNote>[1a, 1c] Pleasingly, the methodology enabled the introduction of substituted piperidines (3ac,ad), 2-methyl-pyrrolidine (3ae), N-Me and N-Cbz-piperazine (3af, ag), morpholine (3ah), thiomorpholine (3ai) and azepine (3aj). Non-cyclic amines were also amenable as demonstrated by the formation of products containing diethyl- (3ak), dibenzyl- (3al) and methyl,ethylbenzyl- (3am) amine residues in high yields. We then decided to benchmark this strategy in the late-stage amination of complex molecules. ADDIN EN.CITE <EndNote><Cite><Author>DiRocco</Author><Year>2014</Year><RecNum>1635</RecNum><DisplayText><style face="superscript">[29]</style></DisplayText><record><rec-number>1635</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1496311892">1635</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>D. A. DiRocco</author><author>K. Dykstra</author><author>S. Krska</author><author>P. Vachal</author><author>D. V. Conway</author><author>M. Tudge</author></authors></contributors><titles><title>Late-Stage Functionalization of Biologically Active Heterocycles
Through Photoredox Catalysis</title><secondary-title>Angew. Chem. Int. Ed.</secondary-title></titles><periodical><full-title>Angew. Chem. Int. Ed.</full-title></periodical><pages>4802</pages><volume>53</volume><dates><year>2014</year></dates><urls></urls></record></Cite></EndNote>[29] To highlight this possibility, we have selected substrates with broad utility as templates for chiral catalyst design, commercially available blockbuster drugs, natural products and molecular switches. As described in Scheme 3, we performed the selective C–4 amination of a binol derivative (3an), which opens access to a novel class of chiral catalysts. We then showcased the power of the approach with the selective “piperidination” of an acid labile thioglucoside (3ao) as well as the antifungal tolnaftate (3ap), the NSAIDs nabumetone (3aq), which was also run on a gram scale, and indometacin (3ar), the lipid lowering drug gemfibrozil (3as) and the cough suppressant and sedative dextromethorphan (3at). As the drugs were all used without any pre-functionalization at the aromatic unit and in equimolar amount and the reaction displayed excellent selectivity, we believe that this approach has the premise to become a useful tool in the rapid assembly of drug-libraries. Regarding natural products, we successfully introduced the piperidine ring onto the highly complex venom alkaloid strychnine (3au), which contains many redox-active functionalities. Furthermore, we were able to perform amination of azobenzene (3av) that is used as molecular switch in supramolecular chemistry as well as optopharmacology. ADDIN EN.CITE <EndNote><Cite><Author>Garcia-Amoros</Author><Year>2012</Year><RecNum>1723</RecNum><DisplayText><style face="superscript">[30]</style></DisplayText><record><rec-number>1723</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1501744464">1723</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors><authors><author>J. Garcia-Amoros</author><author>D. Velasco</author></authors></contributors><titles><secondary-title>Beilstein J. Org. Chem.</secondary-title></titles><periodical><full-title>Beilstein J. Org. Chem.</full-title></periodical><pages>1003</pages><volume>8</volume><dates><year>2012</year></dates><urls></urls></record></Cite></EndNote>[30] We also evaluated the late-stage arylation of bioactive secondary amines. In this case, we have successfully modified the anti-depressant fluoxetine (3aw), and the Alzheimer’s disease palliative donepezil, which underwent arylation with naphthalene in good yields (3ax). Finally we used this method to “click” two biologically active molecules and form “two-drugs-in-one” hybrids as shown by the “fluoxetination” of nabumetone (3ay) and the “donepezilation” of indometacin (3az).Scheme 3. Scope of the process. Cbz = carboxybenzyl.In conclusion, we have developed a powerful and selective strategy for the amination of aromatics via aminium radicals. This approach provides fast access to aryl amines using un-functionalized aromatics in just 15 minutes. The generality of the process has been illustrated through the late-stage modification of chiral catalyst templates, blockbuster drugs, natural products and photo-switches.Acknowledgements D. L. thanks the European Union for a Career Integration Grant (PCIG13-GA-2013-631556) and EPSRC for a research grant (EP/P004997/1). A. R. thanks the Marie Curie Actions for a Fellowship (703238). Keywords: aryl amine ? aminium radicals ? N-arylation ? late-stage amination ADDIN EN.REFLIST [1](a) E. Vitaku, D. T. Smith, J. T. Njardarson, J. Med. Chem. 2014, 57, 10257-10274; (b) N. A. McGrath, M. Brichacek, J. T. Njardarson, J. Chem. Ed. 2010, 87, 1348; (c) M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol. 2010, 14, 347; (d) S. Hirata, K. Totani, J. Zhang, T. Yamashita, H. Kaji, S. R. Marder, T. Watanabe, C. Adachi, Adv. Funct. Mater. 2013, 23, 3386.[2]C. Sambiagio, S. P. Marsden, A. J. Blacker, P. C. McGowan, Chem. Soc. Rev. 2014, 43, 3525.[3](a) A. S. Guram, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 7901; (b) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131; (c) F. Paul, J. Patt, J. F. Hartwig, J. Am. Chem. Soc. 1994, 116, 5969; (d) J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534. For a dual photoredox-Ni process, see: (e) E. B. Corcoran, M. T. Pirnot, S. Lin, S. D. Dreher, D. A. DiRocco, I. W. Davies, S. L. Buchwald, S. W. C. MacMillan, Science 2016, 353, 279.[4](a) D. M. T. Chan, K. L. Monaco, R. P. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933; (b) D. A. Evans, J. L. Katz, T. R. West, Tetrahedron Lett. 1998, 39, 2937; (c) P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; (d) R. P. Rucker, A. M. Whittaker, H. Dang, G. Lalic, Angew. Chem. Int. Ed. 2012, 51, 3953; (e) W.-J. Yoo, T. Tsukamoto, S. Kobayashi, Angew. Chem. Int. Ed. 2015, 127, 6687; (f) J. C. Vantourout, H. N. Miras, A. Isidro-Llobet, S. Sproules, A. J. B. Watson, J. Am. Chem. Soc. 2017, 139, 4769.[5](a) A. H. Sandtorv, D. R. Stuart, Angew. Chem. Int. Ed. 2016, 128, 16044; (b) Z. Zhou, Z. Ma, N. E. Behnke, H. Gao, L. Kürti, J. Am. Chem. Soc. 2017, 139, 115; (c) T. J. Barker, E. R. Jarvo, J. Am. Chem. Soc. 2009, 131, 15598; (d) T. D. Quach, R. A. Batey, Org. Lett. 2003, 5, 4397.[6](a) F. Collet, R. H. Dodd, P. Dauban, Chem. Commun. 2009, 5061; (b) J. Jiao, K. Murakami, K. Itami, ACS Catal. 2016, 6, 610; (c) J. He, T. Shigenari, J.-Q. Yu, Angew. Chem. Int. Ed. 2015, 127, 6645; (d) L. Legnani, G. P. Cerai, B. Morandi, ACS Catal. 2016, 6, 8162.[7]S. Z. Zard, Chem. Soc. Rev. 2008, 37, 1603-1618.[8]Reviews: (a) C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322-5363; (b) K. L. Skubi, T. R. Blum, T. P. Yoon, Chem. Rev. 2016, 116, 10035; (c) N. A. Romero, D. A. Nicewicz, Chem. Rev. 2016, 116, 10075; (d) J. J. Douglas, M. J. Sevrin, C. R. J. Stephenson, Org. Process. Res. Dev. 2016, 20, 1134; (e) M. N. Hopkinson, B. Sahoo, J.-L. Li, F. Glorius, Chem. Eur. J. 2014, 20, 3874.[9]A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2015, 55, 58-102.[10]Review: (a) J.-R. Chen, X.-Q. Hu, L. Q. Lu, W.-J. Xiao, Chem. Soc. Rev. 2016, 2044-2056. Selected examples: (b) S. Maity, N. Zheng, Angew. Chem. Int. Ed. 2012, 51, 9562; (c) G. Cecere, C. M. Konig, J. L. Alleva, D. W. C. MacMillan, J. Am. Chem. Soc. 2013, 135, 11521; (d) A. J. Musacchio, L. Q. Nguyen, H. Beard, R. R. Knowles, J. Am. Chem. Soc. 2014, 136, 12217; (e) K. Miyazawa, T. Koike, M. Akita, Chem. Eur. J. 2015, 21, 11677; (f) X.-Q. Hu, X. Qi, J.-R. Chen, Q.-Q. Zhao, Q. Wei, W.-J. Xiao, Nat. Com. 2016, 7, 11188; (g) J. C. K. Chu, T. Rovis, Nature 2016, 539, 272-275; (h) H. Jiang, X. An, K. Tong, T. Zheng, Y. Zhang, S. Yu, Angew. Chem. Int. Ed. 2015, 54, 4055; (i) A. J. Musacchio, B. C. Lainhart, X. Zhang, S. G. Naguib, T. C. Sherwood, R. R. Knowles, Science 2017, 355, 727; (j) W. Shu, C. Nevado, Angew. Chem. Int. Ed. 2017, 56, 1881; (k) P. Becker, T. Duhamel, C. J. Stein, M. Reiher, K. Muniz, Angew. Chem. Int. Ed. 2017, 56, 8004; (l) E. A. Wappes, S. C. Fosu, T. C. Chopko, D. A. Nagib, Angew. Chem. Int. Ed. 2016, 128, 10128.[11](a) L. J. Allen, P. J. Cabrera, M. Lee, M. S. Sanford, J. Am. Chem. Soc. 2014, 136, 5607; (b) T. W. Greulich, C. G. Daniluc, A. Studer, Org. Lett. 2015, 17, 254; (c) J. Davies, T. D. Svejstrup, D. F. Reina, N. S. Sheikh, D. Leonori, J. Am. Chem. Soc. 2016, 138, 8092; (d) T. Yamaguchi, E. Yamaguchi, A. Itoh, Org. Lett. 2017, 19, 1282; (e) C. B. Tripathi, T. Ohtani, M. T. Corbetta, T. Ooi, Chem. Sci. 2017, 8, 5622.[12](a) Q. Qin, S. Yu, Org. Lett. 2014, 16, 3504; (b) A. U. Meyer, A. L. Berger, B. Konig, Chem. Commun. 2016, 52, 10918; (c) E. Ito, T. Fukushima, T. Kawakami, K. Murakami, K. Itami, Chem 2017, 2, 383.[13](a) C. J. Michiejda, W. P. Hoss, J. Am. Chem. Soc. 1970, 92, 6298; (b) W. C. Danen, F. A. Neugebauer, Angew. Chem. Int. Ed. 1975, 14, 783; (c) Y. L. Chow, W. C. Danen, S. F. Nelsen, D. H. Rosenblatt, Chem. Rev. 1978, 78, 243; (d) J. A. Baban, B. P. Roberts, A. C. H. Tsang, J. Chem. Soc. Chem. Commun. 1985, 955.[14]J. Hioe, D. S?akic?, V. Vrc?ek, H. Zipse, Org. Biomol. Chem. 2015, 13, 157.[15](a) F. Minisci, R. Galli, Tetrahedron Lett. 1965, 8, 433; (b) H. Bock, K.-L. Kompa, Angew. Chem. Int. Ed. 1965, 4, 783; (c) F. Minisci, Synthesis 1973, 1.[16]J. Davies, S. G. Booth, S. Essafi, R. W. A. Dryfe, D. Leonori, Angew. Chem. Int. Ed. 2015, 54, 14017.[17]B. D. Wagner, G. Ruel, J. Lusztyk, J. Am. Chem. Soc. 1996, 118, 13.[18](a) R. W. Lockhart, R. W. Snyder, Y. L. Chow, J. Chem. Soc. Chem. Commun. 1976, 52; (b) P. Xu, G. Wang, Y. Zhu, W. Li, Y. Cheng, S. Li, C. Zhu, Angew. Chem. Int. Ed. 2015, 128, 2992.[19]S. Fukuzumi, K. Ishikawa, K. Hironaka, T. Tanaka, J. Chem. Soc., Perkin Trans. 2 1986, 751.[20](a) N. A. Romero, K. A. Margrey, N. E. Tay, D. A. Nicewicz, Science 2015, 349, 1326; (b) L. Niu, H. Yi, S. Wang, T. Liu, J. Liu, A. Lei, Nat. Com. 2017, 8, 1.[21]See SI for more information.[22]Quantum yields were determined for the reactions to be > 40 which is in agreement with the presence of "dark" reactivity pathways.[21][23]For example, the "dark" reactions on dibenzyl gave 3c in 45% and on strychnine gave 3au in 6%.[21][23]J. A. C. C. R. Bock, A. R. Gutierrez, T. J. Meyer, D. G. Whitten, B. P. Sullivan, J. K. Nagle, J. Am. Chem. Soc. 1979, 101, 4815.[24]We have screened several electron relay catalysts, and found that 3a could be obtained albeit in considerably lower yields. ADDIN EN.CITE <EndNote><Cite><RecNum>1404</RecNum><DisplayText><style face="superscript">[21]</style></DisplayText><record><rec-number>1404</rec-number><foreign-keys><key app="EN" db-id="f9arva0tlwwezbewzd8prsrtvefxvzesw2w2" timestamp="1460717634">1404</key></foreign-keys><ref-type name="Journal Article">17</ref-type><contributors></contributors><titles></titles><pages>See SI for more information.</pages><dates></dates><urls></urls></record></Cite></EndNote>[21] For example, the dark reaction of 1a and 2 using Fe(bpy)3(PF6)2 (2 mol%) and HClO4 (2.0 equiv.) gave 3a in 40% yield.[21] For other examples of transition metals complexes acting as electron relay catalysts, see: (a) G. B. Boursalian, M.-Y. Ngai, K. N. Hojczyk, T. Ritter, J. Am. Chem. Soc. 2013, 135, 13278; (b) K. Foo, E. Sella, I. Thomé, M. D. Eastgate, P. S. Baran, J. Am. Chem. Soc. 2014, 136, 5279; (c) G. B. Boursalian, W. S. Ham, A. R. Mazzotti, T. Ritter, 2016.[25]S. Fukuzumi, M. Chiba, T. Tanaka, Chem. Lett. 1989, 31.[26]H. G. Roth, N. A. Romero, D. A. Nicewicz, Synlett 2016, 27, 714.[27]J. Cheng, X. Deng, G. Wang, Y. Li, X. Cheng, G. Li, Org. Lett. 2016, 18, 4538.[28]D. A. DiRocco, K. Dykstra, S. Krska, P. Vachal, D. V. Conway, M. Tudge, Angew. Chem. Int. Ed. 2014, 53, 4802.[29]J. Garcia-Amoros, D. Velasco, Beilstein J. Org. Chem. 2012, 8, 1003.Entry for the Table of Contents (Please choose one layout)Layout 1:COMMUNICATIONText for Table of Contents-6731097790((Insert TOC Graphic here))00((Insert TOC Graphic here))Author(s), Corresponding Author(s)*Page No. – Page No.TitleLayout 2:COMMUNICATION-736607302500Text for Table of ContentsThomas D. Svejstrup, Alessandro Ruffoni, Fabio Juliá, Valentin M. Aubert and Daniele Leonori*Page No. – Page No.Synthesis of Arylamines via Aminium Radicals ADDIN EN.REFLIST [1](a) E. Vitaku, D. T. Smith, J. T. Njardarson, J. Med. Chem. 2014, 57, 10257-10274; (b) N. A. McGrath, M. Brichacek, J. T. Njardarson, J. Chem. Ed. 2010, 87, 1348; (c) M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol. 2010, 14, 347; (d) S. Hirata, K. Totani, J. Zhang, T. Yamashita, H. Kaji, S. R. Marder, T. Watanabe, C. Adachi, Adv. Funct. Mater. 2013, 23, 3386.[2]C. Sambiagio, S. P. Marsden, A. J. Blacker, P. C. McGowan, Chem. Soc. Rev. 2014, 43, 3525.[3](a) A. S. Guram, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 7901; (b) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131; (c) F. Paul, J. Patt, J. F. Hartwig, J. Am. Chem. Soc. 1994, 116, 5969; (d) J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534.[4](a) D. M. T. Chan, K. L. Monaco, R. P. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933; (b) D. A. Evans, J. L. Katz, T. R. West, Tetrahedron Lett. 1998, 39, 2937; (c) P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941; (d) R. P. Rucker, A. M. Whittaker, H. Dang, G. Lalic, Angew. Chem. Int. Ed. 2012, 51, 3953; (e) W.-J. Yoo, T. Tsukamoto, S. Kobayashi, Angew. Chem. Int. Ed. 2015, 127, 6687; (f) J. C. Vantourout, H. N. Miras, A. Isidro-Llobet, S. Sproules, A. J. B. Watson, J. Am. Chem. Soc. 2017, 139, 4769.[5](a) A. H. Sandtorv, D. R. Stuart, Angew. Chem. Int. Ed. 2016, 128, 16044; (b) Z. Zhou, Z. Ma, N. E. Behnke, H. Gao, L. Kürti, J. Am. Chem. Soc. 2017, 139, 115; (c) T. J. Barker, E. R. Jarvo, J. Am. Chem. Soc. 2009, 131, 15598; (d) T. D. Quach, R. A. Batey, Org. Lett. 2003, 5, 4397.[6](a) F. Collet, R. H. Dodd, P. Dauban, Chem. Commun. 2009, 5061; (b) J. Jiao, K. Murakami, K. Itami, ACS Catal. 2016, 6, 610; (c) J. He, T. Shigenari, J.-Q. Yu, Angew. Chem. Int. Ed. 2015, 127, 6645; (d) L. Legnani, G. P. Cerai, B. Morandi, ACS Catal. 2016, 6, 8162.[7]S. Z. Zard, Chem. Soc. Rev. 2008, 37, 1603-1618.[8](a) C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322-5363; (b) K. L. Skubi, T. R. Blum, T. P. Yoon, Chem. Rev. 2016, 116, 10035; (c) N. A. Romero, D. A. Nicewicz, Chem. Rev. 2016, 116, 10075; (d) J. J. Douglas, M. J. Sevrin, C. R. J. Stephenson, Org. Process. Res. Dev. 2016, 20, 1134; (e) M. N. Hopkinson, B. Sahoo, J.-L. Li, F. Glorius, Chem. Eur. J. 2014, 20, 3874.[9]A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2015, 55, 58-102.[10](a) J.-R. Chen, X.-Q. Hu, L. Q. Lu, W.-J. Xiao, Chem. Soc. Rev. 2016, 2044-2056; (b) S. Maity, N. Zheng, Angew. Chem. Int. Ed. 2012, 51, 9562; (c) G. Cecere, C. M. Konig, J. L. Alleva, D. W. C. MacMillan, J. Am. Chem. Soc. 2013, 135, 11521; (d) A. J. Musacchio, L. Q. Nguyen, H. Beard, R. R. Knowles, J. Am. Chem. Soc. 2014, 136, 12217; (e) K. Miyazawa, T. Koike, M. Akita, Chem. Eur. J. 2015, 21, 11677; (f) X.-Q. Hu, X. Qi, J.-R. Chen, Q.-Q. Zhao, Q. Wei, W.-J. Xiao, Nat. Com. 2016, 7, 11188; (g) J. C. K. Chu, T. Rovis, Nature 2016, 539, 272-275; (h) H. Jiang, X. An, K. Tong, T. Zheng, Y. Zhang, S. Yu, Angew. Chem. Int. Ed. 2015, 54, 4055; (i) A. J. Musacchio, B. C. Lainhart, X. Zhang, S. G. Naguib, T. C. Sherwood, R. R. Knowles, Science 2017, 355, 727; (j) W. Shu, C. Nevado, Angew. Chem. Int. Ed. 2017, 56, 1881; (k) P. Becker, T. Duhamel, C. J. Stein, M. Reiher, K. Muniz, Angew. Chem. Int. Ed. 2017, 56, 8004; (l) E. A. Wappes, S. C. Fosu, T. C. Chopko, D. A. Nagib, Angew. Chem. Int. Ed. 2016, 128, 10128.[11](a) L. J. Allen, P. J. Cabrera, M. Lee, M. S. Sanford, J. Am. Chem. Soc. 2014, 136, 5607; (b) T. W. Greulich, C. G. Daniluc, A. Studer, Org. Lett. 2015, 17, 254; (c) J. Davies, T. D. Svejstrup, D. F. Reina, N. S. Sheikh, D. Leonori, J. Am. Chem. Soc. 2016, 138, 8092; (d) T. Yamaguchi, E. Yamaguchi, A. Itoh, Org. Lett. 2017, 19, 1282; (e) C. B. Tripathi, T. Ohtani, M. T. Corbetta, T. Ooi, Chem. Sci. 2017, 8, 5622.[12](a) Q. Qin, S. Yu, Org. Lett. 2014, 16, 3504; (b) A. U. Meyer, A. L. Berger, B. Konig, Chem. Commun. 2016, 52, 10918; (c) E. Ito, T. Fukushima, T. Kawakami, K. Murakami, K. Itami, Chem 2017, 2, 383.[13](a) C. J. Michiejda, W. P. Hoss, J. Am. Chem. Soc. 1970, 92, 6298; (b) W. C. Danen, F. A. Neugebauer, Angew. Chem. Int. Ed. 1975, 14, 783; (c) Y. L. Chow, W. C. Danen, S. F. Nelsen, D. H. Rosenblatt, Chem. Rev. 1978, 78, 243; (d) J. A. Baban, B. P. Roberts, A. C. H. Tsang, J. Chem. Soc. Chem. Commun. 1985, 955.[14]J. Hioe, D. S?akic?, V. Vrc?ek, H. Zipse, Org. Biomol. Chem. 2015, 13, 157.[15](a) F. Minisci, R. Galli, Tetrahedron Lett. 1965, 8, 433; (b) H. Bock, K.-L. Kompa, Angew. Chem. Int. Ed. 1965, 4, 783; (c) F. Minisci, Synthesis 1973, 1.[16]J. Davies, S. G. Booth, S. Essafi, R. W. A. Dryfe, D. Leonori, Angew. Chem. Int. Ed. 2015, 54, 14017.[17]B. D. Wagner, G. Ruel, J. Lusztyk, J. Am. Chem. Soc. 1996, 118, 13.[18](a) R. W. Lockhart, R. W. Snyder, Y. L. Chow, J. Chem. Soc. Chem. Commun. 1976, 52; (b) P. Xu, G. Wang, Y. Zhu, W. Li, Y. Cheng, S. Li, C. Zhu, Angew. Chem. Int. Ed. 2015, 128, 2992.[19]S. Fukuzumi, K. Ishikawa, K. Hironaka, T. Tanaka, J. Chem. Soc., Perkin Trans. 2 1986, 751.[20](a) N. A. Romero, K. A. Margrey, N. E. Tay, D. A. Nicewicz, Science 2015, 349, 1326; (b) L. Niu, H. Yi, S. Wang, T. Liu, J. Liu, A. Lei, Nat. Com. 2017, 8, 1.[21], See SI for more information.[22]Quantum.[23]Dibenzyl.[24]J. A. C. C. R. Bock, A. R. Gutierrez, T. J. Meyer, D. G. Whitten, B. P. Sullivan, J. K. Nagle, J. Am. Chem. Soc. 1979, 101, 4815.[25](a) G. B. Boursalian, M.-Y. Ngai, K. N. Hojczyk, T. Ritter, J. Am. Chem. Soc. 2013, 135, 13278; (b) K. Foo, E. Sella, I. Thomé, M. D. Eastgate, P. S. Baran, J. Am. Chem. Soc. 2014, 136, 5279; (c) G. B. Boursalian, W. S. Ham, A. R. Mazzotti, T. Ritter, 2016.[26]S. Fukuzumi, M. Chiba, T. Tanaka, Chem. Lett. 1989, 31.[27]H. G. Roth, N. A. Romero, D. A. Nicewicz, Synlett 2016, 27, 714.[28]J. Cheng, X. Deng, G. Wang, Y. Li, X. Cheng, G. Li, Org. Lett. 2016, 18, 4538.[29]D. A. DiRocco, K. Dykstra, S. Krska, P. Vachal, D. V. Conway, M. Tudge, Angew. Chem. Int. Ed. 2014, 53, 4802.[30]J. Garcia-Amoros, D. Velasco, Beilstein J. Org. Chem. 2012, 8, 1003. ................
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