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

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A method for dirhodium-catalyzed C(sp3)-H amidation of N,N-dimethylanilines was developed. Chemoselective C(sp3)-H amidation of N-methyl group proceeded exclusively in the presence of C(sp2)-H bonds of the electron-rich aromatic ring. Site-selective… Click to show full abstract

A method for dirhodium-catalyzed C(sp3)-H amidation of N,N-dimethylanilines was developed. Chemoselective C(sp3)-H amidation of N-methyl group proceeded exclusively in the presence of C(sp2)-H bonds of the electron-rich aromatic ring. Site-selective C(sp3)-H amidation proceeded exclusively at the N-methyl group of N-methyl-N-alkylaniline derivatives with secondary, tertiary, and benzylic C(sp3)-H bonds α to a nitrogen atom.

Keywords: site selective; sp3 amidation; amidation; dirhodium catalyzed

Journal Title: Synlett
Year Published: 2020

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