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

HJ Xu, YQ Zhao, T Feng, YS Feng

Index: Xu, Hua-Jian; Zhao, Yong-Qiang; Feng, Teng; Feng, Yi-Si Journal of Organic Chemistry, 2012 , vol. 77, # 6 p. 2878 - 2884

Full Text: HTML

Citation Number: 74

Abstract

In this work, an efficient CuSO4-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 CuSO4 as the catalyst and inexpensive 1, 10-phen· H2O as the ligand. Moreover, this catalytic system used environment-friendly solvent (EtOH) and oxidant (oxygen).

~71%

~55%

~69%

~41%

~84%

~82%

~57%

~72%

~81%

~54%

~85%

~78%

~72%

~58%

~66%

~73%

Efficient copper-catalyzed C–S cross-coupling of heterocycli...

[Niu, Liang-Feng; Cai, Yan; Liang, Chao; Hui, Xin-Ping; Xu, Peng-Fei Tetrahedron, 2011 , vol. 67, # 16 p. 2878 - 2881]

Copper-catalyzed direct thiolation of xanthines and related ...

[He, Zuying; Luo, Fang; Li, Yinglong; Zhu, Gangguo Tetrahedron Letters, 2013 , vol. 54, # 44 p. 5907 - 5910]

Simple and efficient copper-catalyzed S-arylation of diaryl ...

[Yasuike, Shuji; Nishioka, Motokazu; Kakusawa, Naoki; Kurita, Jyoji Tetrahedron Letters, 2011 , vol. 52, # 48 p. 6403 - 6406]

N-heterocyclic carbene copper (I) complex-catalyzed direct C...

[Inomata, Hiroshi; Toh, Ayumi; Mitsui, Takashi; Fukuzawa, Shin-Ichi Tetrahedron Letters, 2013 , vol. 54, # 35 p. 4729 - 4731]

Rhodium-catalyzed phenylthiolation reaction of heteroaromati...

[Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko Tetrahedron Letters, 2011 , vol. 52, # 18 p. 2344 - 2347]