Development of a General and Practical Iron Nitrate/TEMPO-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes/Ketones: Catalysis with Table Salt

Oxidation of alcohols is a fundamental transformation related to our daily life. Traditional approaches with at least one stoichiometric amount of oxidants are expensive and cause serious environmental burdens. There are many reports on the aerobic oxidation of simple alcohols such as alkyl or pheny...

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Published in:Advanced synthesis & catalysis 2011-04, Vol.353 (6), p.1005-1017
Main Authors: Ma, Shengming, Liu, Jinxian, Li, Suhua, Chen, Bo, Cheng, Jiajia, Kuang, Jinqiang, Liu, Yu, Wan, Baoqiang, Wang, Yuli, Ye, Juntao, Yu, Qiong, Yuan, Weiming, Yu, Shichao
Format: Article
Language:English
Subjects:
aerobic oxidation
Alcohols
Aldehydes
Byproducts
Catalysis
Chemistry
Exact sciences and technology
General and physical chemistry
iron nitrate
Ketones
Kinetics and mechanisms
Organic chemistry
Oxidants
Oxidation
Oxidizing agents
Reactivity and mechanisms
TEMPO
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Oxidation of alcohols is a fundamental transformation related to our daily life. Traditional approaches with at least one stoichiometric amount of oxidants are expensive and cause serious environmental burdens. There are many reports on the aerobic oxidation of simple alcohols such as alkyl or phenyl carbinols and allylic alcohols, which used oxygen or air as the environmentally benign oxidant forming water as the only by‐product. However, no such protocol has been reported for allenols and propargylic alcohols. Thus, it still highly desirable to develop efficient room temperature oxidations of alcohols with a wide scope including allenols and propargylic alcohols. In this paper, an efficient and clean aerobic oxidation of so far the widest spectrum of alcohols using 1 atm of oxygen or air, producing aldehydes/ketones at room temperature in fairly high isolated yields mostly within a couple of hours is described. It is interesting to observe that the reaction has been efficiently expedited by a catalytic amount of sodium chloride in easily recoverable 1,2‐dichloroethane. A mechanism involving NO and NO2 has been proposed based on the results of the control experiments and GC‐MS studies of the in‐situ formed gas phase of the reaction mixture.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201100033