Practical Cu(OAc)2/TEMPO-catalyzed selective aerobic alcohol oxidation under ambient conditions in aqueous acetonitrile
作者:Jian-An Jiang、Jia-Lei Du、Zhan-Guo Wang、Zhong-Nan Zhang、Xi Xu、Gan-Lin Zheng、Ya-Fei Ji
DOI:10.1016/j.tetlet.2013.09.050
日期:2014.3
We reported a ligand- and additive-free Cu(OAc)(2)/TEMPO catalyst system that enables efficient and selective aerobic oxidation of a broad range of primary and secondary benzylic alcohols, primary and secondary 1-heteroaryl alcohols, cinnamyl alcohols, and aliphatic alcohols to the corresponding aldehydes and ketones. This ambient temperature oxidation protocol is of practical features like aqueous acetonitrile as solvent, ambient air as the terminal oxidant, and low catalyst loading, presenting a potential value in terms of both economical and environmental considerations. Based on the experimental observations, a plausible reaction mechanism was proposed. (C) 2013 Elsevier Ltd. All rights reserved.