Redox-Neutral Decarboxylative and Desulfonylative C(sp3) Trifluoromethylation: Method Development and Mechanistic Inquiry

Chris M Seong; Courtney C Roberts

doi:10.1021/acs.joc.3c00872

Redox-Neutral Decarboxylative and Desulfonylative C(sp³) Trifluoromethylation: Method Development and Mechanistic Inquiry

J Org Chem. 2023 Jul 19. doi: 10.1021/acs.joc.3c00872. Online ahead of print.

Authors

Chris M Seong¹, Courtney C Roberts¹

Affiliation

¹ University of Minnesota, Department of Chemistry, Minneapolis, Minnesota 55455, United States.

PMID: 37467365
DOI: 10.1021/acs.joc.3c00872

Abstract

Sodium triflinate (CF₃SO₂Na) is an inexpensive bench-stable radical CF₃ source that is often activated by external oxidants such as peroxides. However, despite the commercial accessibility of CF₃SO₂Na, the salt has never been applied to decarboxylative trifluoromethylation due to challenges in controlled cross-radical coupling. We report a redox-neutral approach to decarboxylative C(sp³) trifluoromethylation of carboxylic acid derivatives. Mechanistic inquiry is performed to address the limitations in scope.