Catalytic Generation of Carbanions through Carbonyl Umpolung

Wang, Shun and Koenig, Burkhard (2021) Catalytic Generation of Carbanions through Carbonyl Umpolung. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 60 (40). pp. 21624-21634. ISSN 1433-7851, 1521-3773

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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.

Item Type: Article
Uncontrolled Keywords: WOLFF-KISHNER REDUCTION; ALDEHYDE TOSYLHYDRAZONES; ELECTROORGANIC CHEMISTRY; ACTIVATED KETONES; PINACOL; IMINES; PHOTOREDUCTION; CYCLIZATIONS; ALKYLATION; REACTIVITY; carbanions; photocatalysis; Umpolung; Wolff-Kishner reaction
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Petra Gürster
Date Deposited: 20 Dec 2022 07:16
Last Modified: 20 Dec 2022 07:16
URI: https://pred.uni-regensburg.de/id/eprint/46084

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