Copper-catalyzed transformation of ketones to amides via C(CO)–C(alkyl) bond cleavage directed by picolinamide?

Organic & Biomolecular Chemistry Pub Date: 2017-08-14 DOI: 10.1039/C7OB01636K

Abstract

Copper catalyzed chemoselective cleavage of the C(CO)–C(alkyl) bond leading to C–N bond formation with chelation assistance of N-containing directing groups is described. Inexpensive Cu(II)-acetate serves as a convenient catalyst for this transformation. This method highlights the emerging strategy to transform unactivated alkyl ketones into amides in organic synthesis and provides a new strategy for C–C bond cleavage.

Graphical abstract: Copper-catalyzed transformation of ketones to amides via C(CO)–C(alkyl) bond cleavage directed by picolinamide
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