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

Organic letters (2011-11-02)
Shulin Chen, Yuan Xu, Xiaobing Wan
RESUMEN

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.

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Sigma-Aldrich
Formamidine acetate salt, 99%
Sigma-Aldrich
Formamidine hydrochloride, 97%