Work

Bi-Catalyzed Trifluoromethylation of C(sp 2 )–H Bonds under Light

Year: 2023

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We disclose a Bi-catalyzed C–H trifluoromethylation of (hetero)arenes using CF 3 SO 2 Cl under light irradiation. The catalytic method permits the direct functionalization of various heterocycles bearing distinct functional groups. The structural and computational studies suggest that the process occurs through an open-shell redox manifold at bismuth, comprising three unusual elementary steps for a main group element. The catalytic cycle starts with rapid oxidative addition of CF 3 SO 2 Cl to a low-valent Bi(I) catalyst, followed by a light-induced homolysis of Bi(III)–O bond to generate a trifluoromethyl radical upon extrusion of SO 2, and is closed with a hydrogen-atom transfer to a Bi(II) radical intermediate.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.3c10333

Authors: Takuya Tsuruta, Davide Spinnato, Hye Won Moon, Markus Leutzsch, Josep Cornella

Institution: Max-Planck-Institut für Kohlenforschung

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,000