Direct condensation of sulfonamide and formamide: NaI-catalyzed synthesis of N-sulfonyl formamidine using TBHP as oxidant.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.

Organic letters 2011 Dec 2

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A new N-sulfonyl formamidine synthesis was developed via NaI-catalyzed direct condensation of sulfonamide and formamide. The green methodology is featured by high atom economy, easily available starting materials, the lack of need for a transition-metal catalyst, no requirement of hazardous reagent, operational simplicity, and good tolerance with diverse functional groups. Mechanistic studies suggest that the protocol proceeds based upon in situ generated TsN·NaI.

Citation

Shulin Chen, Yuan Xu, Xiaobing Wan. Direct condensation of sulfonamide and formamide: NaI-catalyzed synthesis of N-sulfonyl formamidine using TBHP as oxidant. Organic letters. 2011 Dec 2;13(23):6152-5