Premium
Highly Efficient Aerobic Oxidation of Alcohols by Using Less‐Hindered Nitroxyl‐Radical/Copper Catalysis: Optimum Catalyst Combinations and Their Substrate Scope
Author(s) -
Sasano Yusuke,
Kogure Naoki,
Nishiyama Tomohiro,
Nagasawa Shota,
Iwabuchi Yoshiharu
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403245
Subject(s) - catalysis , nitroxyl , substrate (aquarium) , copper , scope (computer science) , chemistry , alcohol oxidation , photochemistry , combinatorial chemistry , organic chemistry , computer science , oceanography , geology , programming language
The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2‐azaadamantane N ‐oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper‐catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom‐rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.