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Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes.

ABSTRACT: A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation; a pathway that is distinct from the single-electron-transfer mechanisms implicated in related decarboxylative elimination reactions.

SUBMITTER: Stanton MP

PROVIDER: S-EPMC10032571 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes.

Stanton Michael P MP Hoover Jessica M JM

The Journal of organic chemistry 20230120 3

A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation; a pathway that is distinct from the single-electron-transfer mechanisms imp ...[more]

PMID: 36662592

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