Transition metal-free decarboxylative olefination of carboxylic acid salts

Abstract

The cost-effective and efficient synthesis of alkenes is highly significant due to their extensive applications in both synthetic and polymer industries. A transition metal-free approach has been devised for the chemoselective olefination of carboxylic acid salts. This modular approach provides direct access to valuable electron-deficient styrenes in moderate to good yields. Detailed mechanistic studies suggest anionic decarboxylation is followed by halogen ion transfer. This halogen transfer leads to an umpolung of reactant electronics, allowing for a rate-limiting rebound elimination.

Graphical abstract: Transition metal-free decarboxylative olefination of carboxylic acid salts

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Mar 2024
Accepted
30 Apr 2024
First published
15 May 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024, Advance Article

Transition metal-free decarboxylative olefination of carboxylic acid salts

E. Joseph, D. S. Brar, G. Stuhlsatz and J. A. Tunge, Chem. Sci., 2024, Advance Article , DOI: 10.1039/D4SC01905A

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