Activation of aryl thiocyanates followed by aryne insertion: access to 1,2-thiobenzonitriles

Organic Letters
Martin PawliczekDaniel B Werz

Abstract

Palladium-catalyzed activation of carbon-sulfur bonds allows aryne insertion into aryl thiocyanates to generate new C-SAr and C-CN bonds in one step. The readily available starting materials make this method efficient in generating a variety of 1,2-thiobenzonitriles. By choosing an oxygen atmosphere the yields are increased and side reactions are minimized.

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Citations

Mar 13, 2015·The Journal of Organic Chemistry·Jan WallbaumDaniel B Werz
Nov 3, 2015·Journal of the American Chemical Society·Suguru YoshidaTakamitsu Hosoya
Mar 30, 2017·The Journal of Organic Chemistry·Manikandan ThangarajAkkattu T Biju
Jan 15, 2016·Angewandte Chemie·Catherine M HoldenMichael F Greaney
Dec 15, 2015·Chemical Communications : Chem Comm·Manikandan ThangarajAkkattu T Biju
Aug 26, 2016·Chemical Communications : Chem Comm·Suguru YoshidaTakamitsu Hosoya
Dec 15, 2015·Chemical Society Reviews·Thomas CastanheiroMihaela Gulea
May 22, 2018·Chemical Communications : Chem Comm·Duo ZhangCarsten Bolm
Aug 16, 2017·Organic & Biomolecular Chemistry·Lei ZhangBo Peng
Feb 21, 2019·Chemical Communications : Chem Comm·Tony RoyAkkattu T Biju
Aug 9, 2019·Chemical Communications : Chem Comm·Yao ZhouQiuling Song
Sep 19, 2019·Angewandte Chemie·Daniel B Werz, Akkattu T Biju
May 28, 2020·Chemical Society Reviews·Jiang LouZhengkun Yu
Jun 26, 2020·Organic & Biomolecular Chemistry·Xiaomin WangQian Zhang

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