Trifluoromethylative and Pentafluoroethylative Heterofunctionalization (C-O, C-S, and C-N) of Alkenes Using Visible Light Photocatalysis

Ye Rin Choi; Seongeun Kang; Junyeon Hwang; Hongchan An; Ki Bum Hong

doi:10.1021/acsomega.4c06017

Trifluoromethylative and Pentafluoroethylative Heterofunctionalization (C-O, C-S, and C-N) of Alkenes Using Visible Light Photocatalysis

ACS Omega. 2024 Nov 19;9(48):47500-47505. doi: 10.1021/acsomega.4c06017. eCollection 2024 Dec 3.

Authors

Ye Rin Choi¹, Seongeun Kang¹, Junyeon Hwang¹, Hongchan An^{1

2}, Ki Bum Hong¹

Affiliations

¹ New Drug Development Center (NDDC), Daegu-Gyeongbuk Medical Innovation Foundation (DGMIF), 80 Cheombok-ro, Dong-gu, Daegu 41061, Republic of Korea.
² College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon-si, Gyeonggi-do 11160, Republic of Korea.

Abstract

A mild and general method for photoredox-catalyzed trifluoromethylative and pentafluoroethylative heterofunctionalization of alkenes is proposed. In this reaction, the Togni reagent serves as a CF₃- or CF₂CF₃-radical source for the regioselective formation of the C-CF₃ and C-CF₂CF₃ bonds from alkenes, and additional nucleophiles (O, S, N) provide C-O, C-S, and C-N bonds, respectively. These reactions provide a common gateway to access the fluoroalkylative heterofunctionalization of alkenes.