Abstract
Carbonyl Umpolung is a powerful strategy in organic chemistry to construct complex molecules. Over the last few years, versatile catalytic approaches for the generation of acyl anion equivalents from carbonyl compounds have been developed, but methods to obtain alkyl carbanions from carbonyl compounds in a catalytic fashion are still at an early stage. This Minireview summarizes recent progress in the generation of alkyl carbanions through catalytic carbonyl Umpolung. Two different catalytic approaches can be utilized to enable the generation of alkyl carbanions from carbonyl compounds: the catalytic Wolff–Kishner reaction and the catalytic single‐electron reduction of carbonyl compounds and imines. We discuss the reaction scope, mechanistic insights, and synthetic applications of the methods as well as potential future developments.
Highlights
Wolff–Kishner (WK) reduction, in which carbonyl functionalities are converted into methyleneThe concept of Umpolung, first introduced by Wittig[1] groups.[6]
The development of N-heterocyclic carbene (NHC) catalysis provides another valuable and important addition to the chemistry of acyl anion equivalents, with great efforts devoted to the design and synthesis of novel NHC catalysts that catalyze the carbonyl Umpolung reactions.[5]
We have summarized recent advances in the generation of carbanionic intermediates by catalytic carbonyl Umpolung strategies
Summary
Wolff–Kishner (WK) reduction, in which carbonyl functionalities are converted into methylene. The development of N-heterocyclic carbene (NHC) catalysis provides another valuable and important addition to the chemistry of acyl anion equivalents, with great efforts devoted to the design and synthesis of novel NHC catalysts that catalyze the carbonyl Umpolung reactions.[5] The three abovementioned Umpolung strategies constitute the most widely used approaches to access acyl anion species from carbonyl compounds. These seminal discoveries mark true breakthroughs in synthetic method development in the past. Catalytic Methods for the Generation of Alkyl Carbanions from Carbonyl Compounds
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