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Copper-Catalyzed Decarboxylative Functionalization of Conjugated β,γ-Unsaturated Carboxylic Acids.

ABSTRACT: Copper-catalyzed decarboxylative coupling reactions of conjugated β,γ-unsaturated carboxylic acids have been achieved for allylic amination, alkylation, sulfonylation, and phosphinoylation. This approach was effective for a broad scope of amino, alkyl, sulfonyl, and phosphinoyl radical precursors as well as various conjugated β,γ-unsaturated carboxylic acids. These reactions also feature high regioselectivity, good functional group tolerance, and simple operation procedure. Mechanistic studies show that the reaction proceeds via copper-catalyzed electrophilic addition onto an olefin followed by decarboxylation, with radical intermediates involved. These insights present a modular and powerful strategy to access versatilely functionalized allyl-containing skeletons from readily available and stable carboxylic acids.

SUBMITTER: Zhang W

PROVIDER: S-EPMC8346209 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Decarboxylative Functionalization of Conjugated β,γ-Unsaturated Carboxylic Acids.

Zhang Wei W Wang Chengming C Wang Qiu Q

ACS catalysis 20201029 22

Copper-catalyzed decarboxylative coupling reactions of conjugated β,γ-unsaturated carboxylic acids have been achieved for allylic amination, alkylation, sulfonylation, and phosphinoylation. This approach was effective for a broad scope of amino, alkyl, sulfonyl, and phosphinoyl radical precursors as well as various conjugated β,γ-unsaturated carboxylic acids. These reactions also feature high regioselectivity, good functional group tolerance, and simple operation procedure. Mechani ...[more]

PMID: 34367721

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