Visible-Light-Triggered Synthesis of N-α-Ketoacylated Sulfoximines by Denitrogenative and Oxidative Functionalization of Vinyl Azides

J Org Chem. 2024 Jun 7;89(11):8137-8145. doi: 10.1021/acs.joc.4c00796. Epub 2024 May 17.

Abstract

We have introduced a sulfoximidation reaction initiated by visible light between α-phenyl vinyl azides and NH-sulfoximines. The cost-effective and readily accessible hypervalent iodine reagent (PIDA) easily promoted the oxidative sulfoximidation process to afford N-α-ketoacylated sulfoximines in good to high yields, involving the formation of two new C-O bonds and one C-N bond. Additionally, the protocol offers noteworthy advantages, including its metal-free and photocatalyst-free reaction and its broad substrate compatibility.