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  • Synthesis of aryl thioethers through the N-chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents.

Synthesis of aryl thioethers through the N-chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents.

The Journal of organic chemistry (2012-10-17)
Jun-Hao Cheng, Chintakunta Ramesh, Hsin-Lun Kao, Yu-Jen Wang, Chien-Ching Chan, Chin-Fa Lee
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 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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N-Chlorosuccinimide, 98%
Sigma-Aldrich
4-Fluorophenylmagnesium bromide solution, 1.0 M in THF