Metal-Free C-H Sulfamidation of 1,4-Naphthoquinone in Water

Direct sulfamidation of 1,4-naphthoquinones using N-methoxy sulfonamides under metal-free conditions in water was developed. Base-mediated nucleophilic addition of N-methoxy sulfonamides, followed by N-O bond cleavage allowed the formation of enesulfonamides. Further, the synthesis of pyrrolonaphthoquinones proved the practicability of the current approach.

Automated summary

A metal-free direct sulfamidation of 1,4-naphthoquinones using N-methoxy sulfonamides in water was developed. The base-mediated nucleophilic addition of N-methoxy sulfonamides, followed by N-O bond cleavage, allowed the synthesis of enesulfonamides. The practicality of this approach was further demonstrated by the synthesis of pyrrolonaphthoquinones.