Visible-Light-Induced, Catalyst-Free Monofluoromethyl Sulfonylation of Alkenes with Iodine(III) Reagent and DABSO

Zhi-Peng Ye; Jing-Song Yang; Si-Jia Yang; Meng Guo; Chu-Ping Yuan; Yong-Qing Ye; Hong-Bin Chen; Hao-Yue Xiang; Kai Chen; Hua Yang

doi:10.1021/acs.orglett.3c02766

Visible-Light-Induced, Catalyst-Free Monofluoromethyl Sulfonylation of Alkenes with Iodine(III) Reagent and DABSO

Org Lett. 2023 Sep 29;25(38):7062-7066. doi: 10.1021/acs.orglett.3c02766. Epub 2023 Sep 19.

Authors

Zhi-Peng Ye¹, Jing-Song Yang¹, Si-Jia Yang¹, Meng Guo¹, Chu-Ping Yuan¹, Yong-Qing Ye¹, Hong-Bin Chen^{1

2}, Hao-Yue Xiang¹, Kai Chen¹, Hua Yang¹

Affiliations

¹ College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
² Jiangxi Time Chemical Company, Ltd., Fuzhou 344800, P. R. China.

PMID: 37726866
DOI: 10.1021/acs.orglett.3c02766

Abstract

A visible-light-induced radical relay strategy to access heterocycles bearing a monofluoromethylsufonyl moiety is reported, with PhI(OCOCH₂F)₂ as the CH₂F radical precursor and DABSO as the SO₂ source. A range of oxindoles, containing a CH₂FSO₂CH₂- group at the C3 position, were synthesized from N-arylacrylamides in up to 97% yields. The protocol features catalyst-free photochemical tandem, mild reaction conditions, broad functional group compatibility, and good to excellent yields.