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A Highly Practical Copper(II)/TEMPO‐SO 4 H Catalyst System for Aerobic Oxidations of Primary Benzylic and Allylic Alcohols on Gram‐Scale in Water
Author(s) -
Chen Tianyou,
Wang Zihao,
Xiao Juncong,
Cao Zheng,
Yi Changfeng,
Xu Zushun
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900370
Subject(s) - allylic rearrangement , chemistry , catalysis , primary (astronomy) , copper , alcohol oxidation , organic chemistry , open air , dual role , combinatorial chemistry , physics , astronomy , architectural engineering , engineering
Abstract We report a highly practical copper(II)/TEMPO‐SO 4 H catalyst system for aerobic oxidations of primary benzylic and allylic alcohols. A higher activity was achieved when TEMPO‐SO 4 H, an economically feasible 2,2,6,6‐tetramethylpiperidinyl‐1‐oxyl (TEMPO) derivative containing a sulfonic acid group, was used to replace TEMPO. The use of such Cu II /TEMPO‐SO 4 H catalysts can significantly simplify the removal of catalysts and dramatically reduce the amount of organic solvents used. The aerobic oxidation of primary benzylic and allylic alcohols was conducted in water on gram scale using air as the oxidant, and in the absence of surfactant, leading to green catalysis.