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Cuprous Oxide Catalyzed Oxidative CC Bond Cleavage for CN Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
Author(s) -
Wang Min,
Lu Jianmin,
Ma Jiping,
Zhang Zhe,
Wang Feng
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508071
Subject(s) - chemistry , bond cleavage , catalysis , cleavage (geology) , ketone , oxide , oxidative cleavage , medicinal chemistry , photochemistry , organic chemistry , materials science , fracture (geology) , composite material
Selective oxidative cleavage of a CC bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative CC bond cleavage of ketone for CN bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In‐depth studies show that both α‐CH and β‐CH bonds adjacent to the carbonyl groups are indispensable for the CC bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α‐CH bond. Amines lower the activation energy of the CC bond cleavage, and thus promote the reaction. New insight into the CC bond cleavage mechanism is presented.