Synthesis of Aryl Thioethers through the N-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents

JH Cheng, C Ramesh, HL Kao, YJ Wang…

Index: Cheng, Jun-Hao; Ramesh, Chintakunta; Kao, Hsin-Lun; Wang, Yu-Jen; Chan, Chien-Ching; Lee, Chin-Fa Journal of Organic Chemistry, 2012 , vol. 77, # 22 p. 10369 - 10374

Full Text: HTML

Citation Number: 43

Abstract

A convenient one-pot approach for the synthesis of aryl sulfides through the coupling of thiols with Grignard reagents in the presence of N-chlorosuccinimide is described. The sulfenylchlorides were formed when thiols were treated with N-chlorosuccinimide, and the resulting sulfenylchlorides were then directly reacted with Grignard reagents to provide aryl sulfides in good to excellent yields under mild reaction conditions. Functional groups ...

Related Articles:

Efficient copper-catalyzed C–S cross-coupling of heterocyclic thiols with aryl iodides

[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 heterocycles with disulfides

[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 disulfides with triarylbismuthanes under aerobic conditions

[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–H thiolation of benzothiazoles

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

Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio) isobutyrophenone

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

More Articles...