Integrating Radical Deconstruction of the N-N Bond in Sulfonyl Hydrazones and Remote 1,4-Amino Migration to Achieve 1,2-Carboimination of Unactivated Alkenes

Abstract

A photoredox-catalyzed 1,2-carboimination of unactivated alkenes via radical N-N bond cleavage and remote 1,4-amino migration is described. Employing fac-Ir(ppy)3 as catalyst and 1,4-dioxane as solvent and HAT reagent, the reaction enables efficient assembly of structurally diverse imine derivatives from N-homoallylsulfonyl hydrazones and α-carbonyl alkyl bromides under mild conditions. Mechanistic investigations support a radical cascade pathway involving single electron transfer, addition, cyclization, β-scission, and HAT process.