Transition metal-catalyzed carboacylation of alkenes provides an attractive strategy to form two carbon-carbon bonds and rapidly increase molecular complexity in a single transformation. However, most carboacylations of alkenes rely on oxidative addition of an activated carbon-carbon bond or directing groups to facilitate carbon-carbon bond cleavage. This presentation will introduce a complementary approach to carboacylation of alkenes that is initiated by activation of readily available carboxylic acid derivatives, such as an amide or ester, with a nickel catalyst followed by transmetalation with an organometallic nucleophile. Studies to establish the scope of these formal carboacylation reactions will be presented in the context of synthesis of substituted indanones from 2-allylbenzamides and organometallic nucleophiles.

Nickel-catalyzed carboacylation of alkenes via activation of amide C-N bonds

253rd National Meeting (2017)

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