Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes
Keri A. Steiniger, Matthew C. Lamb, Tristan H. Lambert
Abstract
A method for C(sp 3 )–C(sp 3 ) cross-coupling of amines is described. Primary amines are converted to 1,2-dialkyldiazenes by treatment with O -nosylhydroxylamines in the presence of atmospheric oxygen. Denitrogenation of the diazenes with an iridium photocatalyst then forges the C–C bond. The substrate scope accommodates a broad latitude of functionality, including heteroaromatics and unprotected alcohols and acids.
Topics & Concepts
ChemistryIn situPhotocatalysisCoupling (piping)PhotochemistryOrganic chemistryCatalysisMechanical engineeringEngineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions