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Copper- and Ligand-Free Sonogashira Reaction Catalyzed by Pd(0) Nanoparticles at Ambient Conditions under Ultrasound Irradiation

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Atul R. Gholap,^† K. Venkatesan,^† Renu Pasricha,^‡ Thomas Daniel,^† Rajgopal J. Lahoti,^† and Kumar V. Srinivasan*^†

Organic Chemistry; Technology Division, and Centre for Material Characterization, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune - 411 008, India kvsri@dalton.ncl.res.in

J. Org. Chem., 2005, 70 (12), pp 4869–4872

DOI: 10.1021/jo0503815

Publication Date (Web): May 7, 2005

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

The Sonogashira reaction proceeds at ambient temperature (30 °C) in acetone or room-temperature ionic liquid, 1,3-di-n-butylimidazolium tetrafluoroborate ([bbim]BF₄), as solvent under ultrasound irradiation to give enhanced reaction rates, excellent chemoselectivity, and high yields in the absence of a copper cocatalyst and a phosphine ligand. TEM analysis showed the formation of stable, crystalline, and polydispersed Pd(0) nanoparticles as catalyst for the reaction.

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Published In Issue June 10, 2005
Received March 1, 2005

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Copper- and Ligand-Free Sonogashira Reaction Catalyzed by Pd(0) Nanoparticles at Ambient Conditions under Ultrasound Irradiation