Synthesis of aryl tri- and difluoromethyl thioethers via a C-H-thiocyanation/fluoroalkylation cascade

Chemistry : a European Journal
Kévin JouvinLukas J Goossen

Abstract

An AlCl3 -catalyzed CH thiocyanation was discovered and combined with a Langlois-type trifluoromethylation to afford aryl trifluoromethyl thioethers directly from arenes, N-thiocyanatosuccinimide (NTS) and Ruppert-Prakash reagent. An analogous combination with a copper-mediated difluoromethylation gives access to aryl difluoromethyl thioethers. Both processes proceed with exceptional regioselectivity for the most electron-rich, sterically least hindered position of the arene. The sulfur and fluoroalkyl groups originate from different sources, so that the use of expensive, preformed fluoroalkylthiolation reagents is avoided.

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Citations

Apr 29, 2016·Organic Letters·Hélène ChachignonDominique Cahard
Feb 18, 2016·Chemistry : a European Journal·Roman HonekerFrank Glorius
Sep 27, 2016·Angewandte Chemie·Heng-Ying XiongTatiana Besset
Nov 29, 2016·Angewandte Chemie·Longin Justin Clair Bonazaba MilandouSébastien Thibaudeau
Jun 17, 2016·Chemical Communications : Chem Comm·Joseph L HowardDuncan L Browne
May 22, 2018·Chemical Communications : Chem Comm·Duo ZhangCarsten Bolm
Jan 19, 2019·Organic & Biomolecular Chemistry·Xavier Pannecoucke, Tatiana Besset
Apr 3, 2019·Chemical Communications : Chem Comm·Jianjun WangTatiana Besset
Mar 11, 2020·Chemical Communications : Chem Comm·Tianqi DingWenbin Yi
Sep 14, 2016·Chemistry : a European Journal·Heng-Ying XiongTatiana Besset
Aug 8, 2020·Chemistry, an Asian Journal·Akitaka Yokawa, Shigekazu Ito
Jul 6, 2016·Chemistry : a European Journal·Christian MatheisLukas J Goossen
Aug 7, 2018·Chemical Science·Jianbin LiChao-Jun Li
Jun 20, 2020·Beilstein Journal of Organic Chemistry·Louise Ruyet, Tatiana Besset
Aug 25, 2020·Chemistry : a European Journal·Mélissa GaoTatiana Besset
Jan 1, 2021·Chemical Reviews·Pavel K Mykhailiuk
Feb 28, 2019·Bioorganic & Medicinal Chemistry·María N ChaoJuan B Rodriguez
Aug 17, 2017·The Journal of Organic Chemistry·Huanfeng JiangWanqing Wu
Dec 23, 2020·The Journal of Organic Chemistry·Ankun LiXia Zhao
Sep 4, 2021·The Journal of Organic Chemistry·Min ZhangJi-Chang Xiao
Jan 9, 2021·The Journal of Organic Chemistry·Xing-Xing ZhuHua-Jian Xu

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