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Chloroacetate‐Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis
Author(s) -
Liu Jianming,
Zhang Xin,
Yi Hong,
Liu Chao,
Liu Ren,
Zhang Heng,
Zhuo Kelei,
Lei Aiwen
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409580
Subject(s) - chemistry , methylene , copper , catalysis , organic chemistry , combinatorial chemistry
The efficient selective oxidation and functionalization of CH bonds with molecular oxygen and a copper catalyst to prepare the corresponding ketones was achieved with ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process. The N‐heterocyclic compounds and ethyl chloroacetate work synergistically to activate CH bonds in the methylene group, which results in the easy generation of free radical intermediates, thus leading to the corresponding ketones in good yields.