Visible-Light-Induced Radical Carbon Oximation of Styrenes Using N-Nitrosoamine and Organic Halides

J Org Chem. 2024 Dec 23. doi: 10.1021/acs.joc.4c02193. Online ahead of print.

Abstract

An efficient visible-light-induced radical carbon oximation of styrenes with 1-nitrosopyrrolidine and organic halides is developed. The reaction proceeds smoothly in the absence of a transition metal and a photocatalyst under mild conditions, producing a wide range of functionalized oximes in moderate to good yields. Mechanistic studies reveal that the reaction involves the generation of nucleophilic α-amino alkyl radicals and subsequent halogen atom transfer (XAT) with organic halides.