Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ

Angewandte Chemie
Bilguun BayarmagnaiLukas J Goossen

Abstract

A copper-CF2 H complex generated in situ from copper thiocyanate and TMSCF2 H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts. This strategy enables the introduction of difluoromethylthio groups-a largely unexplored substituent with highly promising properties-into drug-like molecules.

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Citations

Jan 13, 2016·Organic Letters·Ya-Mei LinGuo-Ping Lu
Jul 17, 2015·Journal of the American Chemical Society·Dianhu ZhuQilong Shen
Apr 3, 2016·Angewandte Chemie·Ermal IsmalajThierry Billard
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Nov 17, 2017·Angewandte Chemie·Jiao YuJi-Chang Xiao
Jan 19, 2019·Organic & Biomolecular Chemistry·Xavier Pannecoucke, Tatiana Besset
Apr 3, 2019·Chemical Communications : Chem Comm·Jianjun WangTatiana Besset
Jul 17, 2019·Organic & Biomolecular Chemistry·Chengqiu LiFu-Xue Chen
Mar 11, 2020·Chemical Communications : Chem Comm·Tianqi DingWenbin Yi
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Mar 5, 2021·Organic & Biomolecular Chemistry·Qingyun GuXiaobao Zeng
Mar 12, 2021·The Journal of Organic Chemistry·Haopeng WuFu-Xue Chen
Jun 30, 2021·Accounts of Chemical Research·Jiang Wu, Qilong Shen

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