Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis

Chemistry : a European Journal
Roman HonekerFrank Glorius

Abstract

Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical.

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Citations

Apr 26, 2016·Chemical Reviews·Kazimer L SkubiTehshik P Yoon
Dec 10, 2016·Journal of the American Chemical Society·Satobhisha MukherjeeFrank Glorius
Apr 13, 2017·Journal of the American Chemical Society·Mattia SilviVarinder K Aggarwal
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Jun 14, 2016·Organic & Biomolecular Chemistry·Yang YuXin-Shan Ye
Aug 30, 2017·Chemical Communications : Chem Comm·Huan LiFeng-Ling Qing
Jan 19, 2019·Organic & Biomolecular Chemistry·Xavier Pannecoucke, Tatiana Besset
Jan 16, 2019·Chemistry : a European Journal·Clément GhiazzaAnis Tlili
Apr 25, 2019·Chemistry : a European Journal·Caterina ViglianisiStefano Menichetti
Jul 4, 2019·Chemical Society Reviews·Alexey A FestaErik V Van der Eycken
Oct 11, 2019·Beilstein Journal of Organic Chemistry·Xiaowei LiDayong Shi
Mar 13, 2019·Organic & Biomolecular Chemistry·Mei ZhuBaoming Ji
Apr 23, 2020·Beilstein Journal of Organic Chemistry·Ming-Xi BiFeng-Ling Qing
Mar 18, 2021·Beilstein Journal of Organic Chemistry·Xiaojuan LiYi Pan
Jun 15, 2021·Chemical Science·Xueying ZhangZikun Wang
Aug 21, 2021·Angewandte Chemie·Chao-Lai TongFeng-Ling Qing

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