Trifluoromethylthiolation-arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling

Chemical Science
Marvin LübckeKálmán J Szabó

Abstract

A new Zn-mediated trifluoromethylthiolation-based bifunctionalization reaction is developed. In this process, simultaneous C-SCF3 and C-C bond formation takes place in a multicomponent reaction, in which an aryl and a SCF3 group arise from different reagents. Our studies show that the reaction mechanism is similar to the Hooz multicomponent coupling. The process involves in situ generation of BAr3, which reacts with a diazocarbonyl compound, and the reaction is terminated by an electrophilic SCF3 transfer. The reaction can also be extended to fluorination based bifunctionalization which proceeds with somewhat lower yield than the analogous trifluoromethylthiolation reaction.

References

Apr 1, 1979·British Journal of Clinical Pharmacology·T SilverstoneJ Plumley
Feb 1, 1976·British Journal of Clinical Pharmacology·J F GiudicelliA Berdeaux
Sep 14, 2000·Chemistry : a European Journal·A BoudierP Knochel
Mar 6, 2009·Organic Letters·Cheng PengJianbo Wang
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
May 10, 2013·Angewandte Chemie·Anis Tlili, Thierry Billard
Oct 2, 2013·The Journal of Organic Chemistry·Nadia O IlchenkoKálmán J Szabó
Nov 20, 2013·Accounts of Chemical Research·Xin Guo, Wenhao Hu
Jun 19, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Zhi HeAndrei K Yudin
Sep 4, 2014·Chemical Reviews·Chang-Liang Sun, Zhang-Jie Shi
May 8, 2015·Accounts of Chemical Research·Xinxin ShaoQilong Shen
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Jan 6, 2018·Journal of the American Chemical Society·Stefan VerhoogVéronique Gouverneur

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Citations

Oct 19, 2019·Chemical Communications : Chem Comm·Miguel A Cortés GonzálezKálmán J Szabó
Feb 13, 2020·Chemical Communications : Chem Comm·Francesca FrancoAlessandra Lattanzi
Apr 7, 2020·Chemistry, an Asian Journal·Shuai WuCheng-Pan Zhang
Mar 19, 2020·Chemistry : a European Journal·Guillaume PisellaJérôme Waser
Mar 3, 2020·Organic & Biomolecular Chemistry·Priyanka HalderSantosh B Mhaske
Aug 14, 2020·Chemical Communications : Chem Comm·Ming Yu JinJun Joelle Wang
Jun 23, 2020·Chemical Communications : Chem Comm·Hongmei QinZhigang Yang
May 23, 2020·The Journal of Organic Chemistry·Xingguo JiangKálmán J Szabó
Dec 3, 2021·The Journal of Organic Chemistry·Satoshi MizutaTakeshi Ishikawa

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Methods Mentioned

BETA
NMR

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