From S-Fluoroalkylation to Fluoroalkylation–Thiolation: Difunctionalization of Alkenes with Fluoroalkyl Phenyl Sulfones and Thiophenols Enabled by Photoredox Copper Catalysis

From S-Fluoroalkylation to Fluoroalkylation–Thiolation: Difunctionalization of Alkenes with Fluoroalkyl Phenyl Sulfones and Thiophenols Enabled by Photoredox Copper Catalysis Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2025, Volume: 27, Number: 8, Pages: 1884–1888 Pages count : DOI: 10.1021/acs.orglett.5c00102

Authors

Xiao Lin ^1,2 , Wei Zhiqiang ² , Ni Chuanfa ² , Dilman Alexander D. ³ , Hu Jinbo ²

Affiliations

1	College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China
2	State 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 Road, Shanghai 200032, China
3	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, Moscow 119991, Russia

Molecules containing fluoroalkyl and arylthio groups play a pivotal role in pharmaceutical and agrochemical development. The simultaneous introduction of these functional groups through the 1,2-difunctionalization of alkenes is an efficient strategy. Fluoroalkyl phenyl sulfones serve as accessible fluoroalkyl radical precursors; however, their tendency to interact with thiophenol via the electron donor–acceptor interaction mechanism can impede the desired transformation. Through meticulous selection of solvent and base, we successfully utilized copper catalysis to facilitate an alkene-involved three-component reaction. Our work unveils a photoredox copper-catalyzed fluoroalkylation–thiolation of alkenes using various fluoroalkyl phenyl sulfones (such as perfluoroethyl, tetrafluoroethyl, trifluoromethyl, difluoromethyl, difluoroalkyl, and difluorobenzyl). The efficacy of this approach is exemplified by the synthesis of Kengreal derivatives.

Xiao L. , Wei Z. , Ni C. , Dilman A.D. , Hu J.
From S-Fluoroalkylation to Fluoroalkylation–Thiolation: Difunctionalization of Alkenes with Fluoroalkyl Phenyl Sulfones and Thiophenols Enabled by Photoredox Copper Catalysis
Organic Letters. 2025. V.27. N8. P.1884–1888. DOI: 10.1021/acs.orglett.5c00102 WOS OpenAlex

Web of science:	WOS:001423590000001
OpenAlex:	W4407652696

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