Facile Method for the Preparation of Triarylsulfonium Bromides Using Grignard Reagents and Chlorotrimethylsilane as an Activator

Shigeaki Imazeki; Motoshige Sumino; Kazuhito Fukasawa; Masami Ishihara; Takahiko Akiyama

doi:10.1055/s-2004-829113

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Synthesis 2004(10): 1648-1654
DOI: 10.1055/s-2004-829113

PAPER

Facile Method for the Preparation of Triarylsulfonium Bromides Using Grignard Reagents and Chlorotrimethylsilane as an Activator

Shigeaki Imazeki*^a, Motoshige Sumino^a, Kazuhito Fukasawa^a, Masami Ishihara^a, Takahiko Akiyama^b
^a Chemical Products Research Laboratories, Wako Pure Chemical Industries, Ltd., 1633 Matoba, Kawagoe, Saitama 350-1101, Japan
Fax: +81(49)2337953; e-Mail: imazeki.shigeaki@wako-chem.co.jp;
^b Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan

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Publication History

Received 8 March 2004
Publication Date:
23 June 2004 (online)

Abstract
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Abstract

Triarylsulfonium bromides were synthesized by the reaction of diaryl sulfoxides with aryl Grignard reagents in the presence of TMSCl followed by treatment with HBr aqueous solution. Triarylsulfonium bromides bearing three identical substituents on sulfur atom were synthesized by the treatment of dimethyl sulfite or thionyl chloride with 5 equivalents of Grignard reagent in the presence of TMSCl.

Key words

silicon - Grignard reaction - sulfoxide - photo acid generator - coupling

References

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