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Synlett 2011(3): 311-314  
DOI: 10.1055/s-0030-1259322
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Ynones via Recyclable Polystyrene-Supported Palladium(0) Complex Catalyzed Acylation of Terminal Alkynes with Acyl Chlorides under Copper- and Solvent-Free Conditions

Mohammad Bakherad*, Ali Keivanloo, Bahram Bahramian, Saeideh Jajarmi
School of Chemistry, Shahrood University of Technology, Shahrood, Iran
Fax: +98(273)3395441; e-Mail: m.bakherad@yahoo.com;
Further Information

Publication History

Received 31 August 2010
Publication Date:
13 January 2011 (online)

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Abstract

Herein, a highly efficient method for the copper- and solvent-free coupling reaction of acyl chlorides and terminal alkynes catalyzed by 1-phenyl-1,2-propanedione-2-oxime thiosemicarbazone-functionalized polystyrene resin-supported Pd(0) complex is described. Acyl chlorides are easily coupled with terminal alkynes, giving good to high yields in the presence of a low catalyst loading (1 mol% Pd) in Et3N at room temperature under aerobic conditions. After centrifugation, the supported catalyst can be recycled and reused several times with only a slight decrease in activity.

Key words

copper-free - solvent-free - supported catalyst - Sonogashira coupling - acyl chloride - ynone

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