Organoboron/iodide-catalyzed photoredox N-functionalization of NH-sulfoximines/sulfonimidamides

An aminoquinolate diarylboron (AQDAB) and tetrabutylammonium iodide (TBAI) co-catalyzed photoredox process for N-functionalization of NH-sulfoximines/sulfonimidamides has been successfully developed. This protocol can afford the corresponding N-sulfenylated and N-phosphonylated products in good to excellent yields under conditions without metallic (photo)catalysts, external oxidants, or acidic/basic additives. A wide range of functional groups are tolerated, and the N-phosphonylated products of NH-sulfonimidamides have been reported for the first time.

Automated summary

A novel photoredox process using AQDAB and TBAI as co-catalysts has been developed for N-functionalization of NH-sulfoximines/sulfonimidamides. The protocol offers good to excellent yields of N-sulfenylated and N-phosphonylated products without the need for metallic (photo)catalysts, external oxidants, or acidic/basic additives. This method is tolerant to a wide range of functional groups and allows the N-phosphonylation of NH-sulfonimidamides for the first time.