Abstract
C-Alkylations of alkali metal carbanions with olefins, first reported five decades ago, is a class of reaction undergoing a resurgence in organic synthesis in recent years. As opposed to expectations from classical chemistry and transition metal-catalysis, here olefins behave as closed-shell electrophiles. Reactions range from highly reactive alkyllithiums giving rise to anionic polymerization, ...
Abstract
C-Alkylations of alkali metal carbanions with olefins, first reported five decades ago, is a class of reaction undergoing a resurgence in organic synthesis in recent years. As opposed to expectations from classical chemistry and transition metal-catalysis, here olefins behave as closed-shell electrophiles. Reactions range from highly reactive alkyllithiums giving rise to anionic polymerization, to moderately reactive alkyl-potassium or alkylsodium compounds that give rise to defined, controlled and bimolecular chemistry. This review presents a brief historical overview on C-alkylation of alkali metal carbanions with olefins (typically mediated by KOtBu and KHMDS), highlights contemporary applications and features developing mechanistic understanding, thereby serving as a platform for future studies and the widespread use of this class of reaction in organic synthesis.
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