Synthesis 2012; 44(10): 1569-1576
DOI: 10.1055/s-0031-1290811
paper
© Georg Thieme Verlag Stuttgart · New York

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
a   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
,
Xi Xie
a   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
,
Shengming Ma*
a   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
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China, Fax: +86(21)62609305   Email: masm@sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 10 February 2012

Accepted after revision: 04 March 2012

Publication Date:
25 April 2012 (online)


Abstract

A practical aerobic oxidation of propargylic alcohols using Fe(NO3)3⋅9H2O, TEMPO and sodium chloride in toluene at room temperature was applied to various type of propargylic alcohols affording α,β-unsaturated alkynals or alkynones in good to excellent yields. This protocol could be applied in academic laboratories as well as in industrial-scale production.

Supporting Information

 
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