Chan-Lam-type S-arylation of thiols with boronic acids at room temperature

The Journal of Organic Chemistry
Hua-Jian XuYi-Si Feng

Abstract

In this work, an efficient CuSO(4)-catalyzed S-arylation of thiols with aryl and heteroaryl boronic acids at room temperature is established. This catalytic system can tolerate a wide variety of thiols and arylboronic acids in the presence of only 5 mol % of CuSO(4) as the catalyst and inexpensive 1,10-phen·H(2)O as the ligand. Moreover, this catalytic system used environment-friendly solvent (EtOH) and oxidant (oxygen).

References

Jul 13, 2000·Organic Letters·P S HerraduraR K Guy
Jun 22, 2001·Organic Letters·J C Antilla, S L Buchwald
Dec 26, 2001·Chemical Reviews·T Kondo, T A Mitsudo Ta
Aug 3, 2002·Organic Letters·Craig G BatesD Venkataraman
Sep 13, 2002·Journal of the American Chemical Society·Fredric M Menger, Vladimir A Azov
Jan 23, 2004·Chemical Communications : Chem Comm·Jing-Bo LanRu-Gang Xie
Jul 17, 2004·The Journal of Organic Chemistry·Neola F McKinley, Donal F O'Shea
Nov 19, 2004·Organic Letters·Takahiro Itoh, Toshiaki Mase
Jun 17, 2005·Organic Letters·Christian Moessner, Carsten Bolm
Feb 16, 2006·Journal of the American Chemical Society·Manuel A Fernández-RodríguezJohn F Hartwig
Jul 1, 2006·The Journal of Organic Chemistry·Sangit Kumar, Lars Engman
Sep 30, 2006·Chemistry : a European Journal·Manuel A Fernández-RodríguezJohn F Hartwig
Nov 17, 2006·Organic Letters·Ying-Chieh WongChien-Hong Cheng
Dec 2, 2006·The Journal of Organic Chemistry·M Lakshmi KantamBoyapati M Choudary
Jun 8, 2007·Angewandte Chemie·Laxmidhar RoutTharmalingam Punniyamurthy
Jul 28, 2007·Organic Letters·Anirban KarMan Kin Tse
Aug 7, 2007·Organic Letters·Yugen ZhangJackie Y Ying
Nov 2, 2007·Chemical Reviews·Egle M BeccalliSilvia Sottocornola
Mar 5, 2008·Angewandte Chemie·Arkaitz CorreaCarsten Bolm
Mar 22, 2008·Organic Letters·Takayuki TsuritaniToshiaki Mase
Jun 24, 2008·The Journal of Organic Chemistry·Elena SperottoGerard van Koten
Jul 10, 2008·The Journal of Organic Chemistry·Sébastien BénardJieping Zhu
Jan 29, 2009·The Journal of Organic Chemistry·Suribabu JammiTharmalingam Punniyamurthy
Mar 20, 2009·The Journal of Organic Chemistry·V Prakash ReddyK Rama Rao
Apr 7, 2009·The Journal of Organic Chemistry·Chad C Eichman, James P Stambuli

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Citations

Jun 22, 2013·Chemical Reviews·Scott E AllenMarisa C Kozlowski
Oct 27, 2015·The Journal of Organic Chemistry·Kunuru VenkateshamYenamandra Venkateswarlu
Jun 2, 2016·Journal of the American Chemical Society·Jun OhataZachary T Ball
Dec 15, 2016·Journal of the American Chemical Society·Vera HirschbeckIvana Fleischer
Dec 10, 2016·Angewandte Chemie·Min JiangHua Fu
May 30, 2015·Chemical Communications : Chem Comm·Zongjun QiaoXuefeng Jiang
Jun 24, 2016·Chemical Communications : Chem Comm·Minghao Li, Jessica M Hoover
Dec 18, 2014·Organic & Biomolecular Chemistry·Nan SunXinquan Hu
May 26, 2017·Angewandte Chemie·Subhajit BhuniaDawei Ma
Sep 19, 2017·Chemical Communications : Chem Comm·Kazuya KanemotoTakamitsu Hosoya
Apr 17, 2019·Organic & Biomolecular Chemistry·Vahid KhakyzadehSima Darvishi
Nov 20, 2013·Chemical Communications : Chem Comm·Aoife A RyanMathias O Senge
Jul 12, 2019·Beilstein Journal of Organic Chemistry·Emeline BenoitAlexandre Gagnon
Oct 25, 2017·Beilstein Journal of Organic Chemistry·Yanhui GuoJie-Ping Wan
Mar 14, 2020·Organic & Biomolecular Chemistry·Amit BhowmikRodney A Fernandes
Mar 25, 2020·Chemical Communications : Chem Comm·Zhiwei XiaoChao Zheng
Jun 27, 2020·Organic & Biomolecular Chemistry·You ZiIvan Vilotijevic
Sep 13, 2014·Chemical Communications : Chem Comm·D Nageswar RaoParthasarathi Das
Feb 13, 2018·Organic & Biomolecular Chemistry·M L CzyzA Polyzos
Oct 10, 2018·Organic & Biomolecular Chemistry·F OlivitoA Procopio
Oct 10, 2014·Chemical Communications : Chem Comm·Jiwen YuanAiwen Lei
Nov 19, 2020·Organic & Biomolecular Chemistry·Rodney A FernandesSandhya S Yadav
Mar 12, 2019·The Journal of Organic Chemistry·Rina SikariNanda D Paul
Jan 15, 2013·Organometallics·Chaohuang ChenJohn F Hartwig
Jan 19, 2013·The Journal of Organic Chemistry·Ch Durga PrasadSangit Kumar
May 8, 2014·Organic Letters·Yiming LiXuefeng Jiang
Apr 23, 2019·ACS Combinatorial Science·Oleksandr VyhivskyiElena K Beloglazkina
Aug 23, 2019·The Journal of Organic Chemistry·Xing Liu, Zhi-Bing Dong
Nov 27, 2018·Journal of the American Chemical Society·Feng ZhuMaciej A Walczak
Dec 22, 2020·The Journal of Organic Chemistry·Wenqi ZhaoGuo-Jun Deng

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