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Aerobic Oxidation of Propargylic Alcohols to α,β-Unsaturated Alkynals or Alkynones Catalyzed by Fe(NO3)3·9H2O, TEMPO and Sodium Chloride in Toluene

Jinxian Liu, Xi Xie, Shengming Ma*

*Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China, Email: masmsioc.ac.cn

J. Liu, X. Xie, S. Ma, Synthesis, 2012, 44, 1569-1576.

DOI: 10.1055/s-0031-1290811

Abstract

A practical aerobic oxidation of propargylic alcohols using Fe(NO3)3•9H2O, TEMPO and sodium chloride in toluene at room temperature allows the conversion of propargylic alcohols to α,β-unsaturated alkynals or alkynones in good to excellent yields. This protocol can also be applied in industrial-scale production.

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Key Words

aerobic oxidation, oxygen, propargylic alcohols, ketones, catalysis, iron nitrate, TEMPO

ID: J66-Y2012-1500