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 H2 O and Et2 O. The organic layer was washed with brine, dried over Na2 SO4 and purified by column chromatography on silica gel eluting with hexane-EtOAc (4:1) to give the corresponding sulfonamide (213 mg, 84%).
