Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes

A method for C-(sp(3))-C-(sp(3)) cross-couplingof amines is described. Primary amines are converted to 1,2-dialkyldiazenesby treatment with O-nosylhydroxylamines in the presenceof atmospheric oxygen. Denitrogenation of the diazenes with an iridiumphotocatalyst then forges the C-C bond. The substrate scopeaccommodates a broad latitude of functionality, including heteroaromaticsand unprotected alcohols and acids.

Automated summary

This study presents a method for C-(sp(3))-C-(sp(3)) cross-coupling of amines. Primary amines are transformed into 1,2-dialkyldiazenes by reacting with O-nosylhydroxylamines in the presence of atmospheric oxygen. The denitrogenation of diazenes using an iridium photocatalyst forms the C-C bond. The substrate scope is broad, allowing for various functional groups, such as heteroaromatics and unprotected alcohols and acids.