Matching Carbenes and Sulfoximines via Ketenes Generated from a-Diazoketones by Blue Light

Although NH-sulfoximines are known to react with carbenes by deamidation pathways, they can be combined if the latter are generated as transients from diazo compounds under blue light irradiation to undergo rapid Wolff rearrangement to generate reactive ketenes. Subsequent addition of sulfoximines or sulfonimidamides lead to N-acylated products in good to excellent yields. Beneficial are the mild reaction conditions, which neither require the addition of a base nor an oxidant or a metal catalyst.

Automated summary

NH-sulfoximines can react with carbenes generated from diazo compounds under blue light irradiation to undergo rapid Wolff rearrangement and form N-acylated products in good yields. The reaction conditions are mild, and no base, oxidant, or metal catalyst is required.