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Synlett 2007(16): 2501-2504  
DOI: 10.1055/s-2007-986632
LETTER
© Georg Thieme Verlag Stuttgart · New York

Mild and Efficient Indium Metal Catalyzed Synthesis of Sulfonamides and Sulfonic Esters

Joong-Gon Kima, Doo Ok Jang*b,c
a Biotechnology Division, Hanwha Chemical R&D Center, Daejeon 305345, South Korea
b Department of Chemistry, Yonsei University, Wonju 220710, South Korea
c Center for Bioactive Molecular Hybrids, Yonsei University, Seoul 120749, South Korea
Fax: +82(33)7602208; e-Mail: dojang@yonsei.ac.kr;
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Publication History

Received 7 July 2007
Publication Date:
28 August 2007 (online)

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Abstract

A facile and efficient method for synthesizing sulfon­amides was developed using a catalytic amount of indium metal. A wide range of sulfonamides were synthesized in excellent yields using the new process. The method showed a generality for substrates including less nucleophilic and sterically hindered anilines, and it is also applicable for preparing sulfonic esters from sulfonyl chlorides and alcohols.

Key words

sulfonylation - indium - sulfonamides - sulfonic esters - sulfonyl chlorides

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Typical Experimental Procedure: A solution of cyclohexylamine (99 mg, 1 mmol), p-toluenesulfonyl chloride (191 mg, 1 mmol) and indium metal (11.5 mg, 0.1 mmol) in MeCN (3 mL) was stirred at r.t. for 8 h under argon. The mixture was partitioned between H2O and Et2O. The organic layer was washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel eluting with hexane-EtOAc (4:1) to give the corresponding sulfonamide (213 mg, 84%).