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J Org Chem. 2007 May 25;72(11):4288-91. Epub 2007 Apr 21.

Efficient NO equivalent for activation of molecular oxygen and its applications in transition-metal-free catalytic aerobic alcohol oxidation.

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  • 1College of Chemical Engineering and Material Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.


tert-Butyl nitrite (TBN) was identified as an efficient NO equivalent for the activation of molecular oxygen. The unique property of TBN enabled TEMPO-catalyzed aerobic alcohol oxidation to be performed in high-volume efficiency. Up to a 16,000 turnover number was achieved in this transition-metal-free aerobic catalytic system. Under the optimal reaction conditions, various alcohols were converted into their corresponding carbonyl compounds with TEMPO/HBr/TBN as catalyst. The newly developed method was suitable for the oxidation of solid substrate alcohols with high melting point and/or low solubility under the help of minimum solvent to form a slurry.

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