Cuprous Oxide Catalyzed Oxidative CC Bond Cleavage for CN Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines

Abstract

Selective oxidative cleavage of aC À Cb ond offers as traightforwardm ethod to functionalizeo rganic skeletons. Reported herein is the oxidative CÀCbond cleavage of ketone for CÀNb ond formation over ac uprous oxide catalyst with molecular oxygen as the oxidant. Awide range of ketones and amines are converted into cyclic imides with moderate to excellent yields.In-depth studies showthat both a-C À Hand b-C À Hbonds adjacent to the carbonyl groups are indispensable for the CÀCb ond cleavage.D FT calculations indicate the reaction is initiated with the oxidation of the a-CÀHb ond. Amines lower the activation energy of the CÀCbond cleavage, and thus promote the reaction. New insight into the CÀCbond cleavage mechanism is presented.