Synthesis of aryl thioethers through the N-chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents.
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 including ester, fluoro, and chloro are tolerated by the reaction conditions employed. It is important to note that this method has a short reaction time (30 min in total) and represents an alternative approach for the synthesis of aryl sulfides over the existing protocols.
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, Republic of China.
Jun-Hao
JH
Cheng
Chintakunta
C
Ramesh
Hsin-Lun
HL
Kao
Yu-Jen
YJ
Wang
Chien-Ching
CC
Chan
Chin-Fa
CF
Lee
D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D013388:Succinimides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D003432:Cross-Linking Reagents; D007202:Indicators and Reagents; D013388:Succinimides; D013438:Sulfhydryl Compounds; D013440:Sulfides; C015752:N-chlorosuccinimide