Copper(I)-Photocatalyzed Diastereoselective Aziridination of N-Sulfonyl Imines with Vinyl Azides: Application to Benzo[f][1,2,3]oxathiazepines Dioxides and Fused Isoxazolines

An in situ generated photoactive copper(I)-complex-catalyzed aziridination reaction of cyclic N-sulfonyl imines with alpha-aryl-substituted vinyl azides irradiated by blue-LEDs light is reported for the first time. This novel SET process represents a mild, sustainable, and pragmatic method for accessing synthetically resourceful sulfamidate-fused aziridines in acceptable chemical yields with excellent diastereoselectivities. Delightedly, pharmacologically attractive benzo[f][1,2,3]oxathiazepine dioxides and fused isoxazoline frameworks were achieved through our newly developed metal-free based ring-expansion techniques, highlighting the synthetic value of accessed aziridines. Finally, the possible mechanism for [2+1] aza-cyclization was presented based on the conduction of a series of control experiments.

Automated summary

A novel method for the aziridination reaction of cyclic N-sulfonyl imines with alpha-aryl-substituted vinyl azides using an in situ generated photoactive copper(I)-complex as catalyst under blue-LEDs light irradiation is reported. This method is mild, sustainable, and practical, providing the desired sulfamidate-fused aziridines with good yields and excellent diastereoselectivities. The newly developed metal-free ring-expansion techniques allow the synthesis of pharmacologically attractive compounds.