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Synlett 2011(7): 1023-1027  
DOI: 10.1055/s-0030-1259929
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Oxidation and Cyclization of Carbon-Carbon Triple Bonds in Fluorous Media Using Molecular Oxygen

Yanmei Wena,b, Shifa Zhua, Huanfeng Jiang*a, Azhong Wanga, Zhenwang Chena
a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. of China
b College of Science, Guangdong Ocean University, Zhanjiang 524088, P. R. of China
Fax: +86(20)87112906; e-Mail: jianghf@scut.edu.cn;
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Publication History

Received 16 November 2010
Publication Date:
29 March 2011 (online)

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Abstract

An intriguing, facile, and efficient oxidation and cyclization of alkynes catalyzed by Pd(OAc)2 in a fluorous biphasic system of N,N-dimethylacetamide (DMA) and perfluorodecalin directly with molecular oxygen is described, which opens an efficient access to tetrasubstituted furans. Under the optimized conditions, intermolecular reaction between diverse alkynes provides the corresponding mixture of regioisomers with appreciable selectivity. Intramolecular oxidation and cyclization of alkynes are also successfully demonstrated. The reaction proceeds efficiently under mild conditions with atmospheric oxygen as the sole oxidant.

Key words

perfluorodecalin - molecular oxygen - alkynes - palladium-catalyzed - oxidation

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