Photoredox Alkylation of Sulfinylamine Enables the Synthesis of Highly Functionalized Sulfinamides and S(VI) Derivatives

Sulfinamides have widespread applications in organic synthesis, especially for the preparation of S(VI) derivatives such as sulfonimidamide and sulfonimidate ester. The previous methods for the preparation of these compounds are restricted to an aryl substituent or Grignard reagent with limited functional groups. Here, we disclosed a photocatalyzed approach for obtaining these compounds with high functionalization levels. Readily available 1,4-dihydropyridine, which could afford Csp3-centered alkyl radicals reacted smoothly with readily available N-sulfinylamine to produce the corresponding sulfinamides in good yields. Moreover, the produced sulfinamides could be converted to the corresponding sulfonimidamides and sulfonimidate esters by successive addition of halogen reagent and N- or O-centered nucleophiles in one pot. The method not only allowed for the preparation of sulfinamides on a gram scale but also guaranteed the post-modification of a series of drugs or natural products.