Dirhodium-Catalyzed Chemo- and Site-Selective C-H Amidation of N,N-Dialkylanilines

A method for dirhodium-catalyzed C(sp(3))-H amidation of N,N-dimethylanilines was developed. Chemoselective C(sp(3))-H amidation of N-methyl group proceeded exclusively in the presence of C(sp(2))H bonds of the electron-rich aromatic ring. Site-selective C(sp(3))-H amidation proceeded exclusively at the N-methyl group of N-methyl-N-alkylaniline derivatives with secondary, tertiary, and benzylic C(sp(3))-H bonds. to a nitrogen atom.

Automated summary

A method for selective C(sp(3))-H amidation of N,N-dimethylanilines was developed, exclusively targeting the N-methyl group for amidation while leaving the C(sp(2))H bonds on the aromatic ring untouched.