Organometallic Chemistry - UR
[Pages:35]Organometallic Chemistry
Worawan Bhanthumnavin
Department of Chemistry
Chulalongkorn University
Bangkok 10330, Thailand Given as part of the 6th semester organic chemistry course
at the University of Regensburg (May 2008) Under the ASEM-DUO Thailand 2007 exchange program
organoboron, organosilicon
Organoboron compounds
? Revise: what organoboron have you seen before? boranes
Organoboron compounds
? vast array of C-C-forming reactions involving organoborons
? Here: focus on transfer reactions of C moieties from boron to an adjacent C. Examples: transfer of CO, CN, carbanions derived from dichloromethyl methyl ether and dichloromethane, and allyl groups in reactions of allylic boranes with aldehydes.
Preparations
Reaction of Organoborons
Carbonylation
? reaction of organoboranes with carbon monoxide [(?):CO:(+) ], which is an ylide, gives rise to 3 possible rearrangements.
? Depending on reaction conditions, single, double, and triple migrations of groups may occur leading, after appropriate workup, to a variety of aldehydes and ketones as well as primary, secondary, and tertiary alcohols.
Reaction of Organoborons Carbonylation
Synthesis of Aldehydes and Primary Alcohols
? Addition of CO to trialkylboranes leads to the formation of an ate-complex (structure A). Subsequent migration of an R group to the CO ligand yields intermediate B. In the presence of a mild reducing agent, such as lithium trimethoxyaluminum hydride or potassium triisopropoxyborohydride, B is converted to the mono-migration product C.
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