Photoredox-Catalysis Fluorosulfonyldifluoromethylation of Unactivated Alkenes and (Hetero)arenes with ICF2SO2F

Xu-Biao He; Xin Jia; Pin-Qiao Zhao; Zeguo Fang; Feng-Ling Qing

doi:10.1021/acs.orglett.4c02538

Photoredox-Catalysis Fluorosulfonyldifluoromethylation of Unactivated Alkenes and (Hetero)arenes with ICF₂SO₂F

Org Lett. 2024 Aug 16;26(32):6900-6904. doi: 10.1021/acs.orglett.4c02538. Epub 2024 Aug 8.

Authors

Xu-Biao He¹, Xin Jia¹, Pin-Qiao Zhao¹, Zeguo Fang², Feng-Ling Qing¹

Affiliations

¹ Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
² New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, Hubei University of Technology, Wuhan 430068, China.

PMID: 39115249
DOI: 10.1021/acs.orglett.4c02538

Abstract

The fluorosulfonyldifluoromethylation of unactivated alkenes and (hetero)arenes with iododifluoromethanesulfonyl fluoride (ICF₂SO₂F) under visible light photoredox catalysis was successfully developed. Key to the successful fluorosulfonyldifluoromethylation of aromatic compounds was the usage of AgOTf as an additive to promote the formation of the CF₂SO₂F radical. The protocol provided a straightforward way to introduce the interesting and useful CF₂SO₂F group on sp³ and sp² carbons.