Work

Transition metal-free decarboxylative olefination of carboxylic acid salts

Year: 2024

Type: article

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.

Source: Chemical Science

DOI: 10.1039/d4sc01905a

Authors: Ebbin Joseph, Deshkanwar S. Brar, Gaven Stuhlsatz, Jon A. Tunge

Institution: University of Kansas

Language: English

Topic: Physical Organic Chemistry and Reaction Kinetics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Science Foundation, National Institutes of Health, National Center for Research Resources, Division of Chemistry