Zinc 1,1,2,2-Tetrafluoroethanesulfinate: A Synthetically Useful Oxidative and Photoredox Source of the 1,1,2,2-Tetrafluoroethyl Radical

Xinjin Li; Satyajit Majumder; Xiaojun Tang; William R Dolbier Jr

doi:10.1021/acs.joc.3c02948

Zinc 1,1,2,2-Tetrafluoroethanesulfinate: A Synthetically Useful Oxidative and Photoredox Source of the 1,1,2,2-Tetrafluoroethyl Radical

J Org Chem. 2024 Apr 19;89(8):5485-5490. doi: 10.1021/acs.joc.3c02948. Epub 2024 Mar 30.

Authors

Xinjin Li^{1

2}, Satyajit Majumder¹, Xiaojun Tang^{1

3}, William R Dolbier Jr¹

Affiliations

¹ Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
² College of Chemistry and Chemical Engineering, Shandong University of Technology, Zibo, Shandong 255000, China.
³ Department of Chemistry, Shanghai University, Shanghai 200444, China.

PMID: 38554099
DOI: 10.1021/acs.joc.3c02948

Abstract

1,1,2,2-Tetrafluoroethyl-containing molecules are of potential importance in drug discovery, but the efficient synthesis of such compounds is still relatively unexplored due to the lack of readily available reagents for the incorporation of the HCF₂CF₂ group. Herein, we introduce a new reagent, zinc 1,1,2,2-tetrafluoroethanesulfinate, which can be useful for the oxidative tetrafluoroethylation of arylboronic acids and heteroarenes as well as for a novel photoredox, three component hydro-tetrafluoroethylation of two alkenes of complementary reactivity.