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Transition metal-free decarboxylative olefination of carboxylic acid salts

Tunge, Jon A
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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.
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2024-05-15
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Chemical Science
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Chemistry Scholarly Works
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SC-015-D4SC01905A.pdf
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Joseph E, Brar DS, Stuhlsatz G, Tunge JA. Transition metal-free decarboxylative olefination of carboxylic acid salts. Chem Sci. 2024 May 15;15(24):9353-9360. doi: 10.1039/d4sc01905a. PMID: 38903232; PMCID: PMC11186341
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https://hdl.handle.net/1808/35609
DOI
10.1039/d4sc01905a
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