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Silicon-based thiourea-mediated and microwave-assisted thio-Michael addition under solvent-free reaction conditions

Kamalakannan Prabakaran, Machindra Gund, Tae Kyu Kim, Euh Duck Jeong, Chae Young Oh, Fazlur-Rahman Nawaz Khan, and Jong Sung Jin

Organic & Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, Tamil Nadu, 632 014 India

 

E-mail: nawaz_f@yahoo.co.in

Abstract: Silicon-based thiourea (SiliaBond® Thiourea) (Si-THU), a heterogeneous catalyst, has been applied to the highly selective C-S bond formation via Michael addition of thiols to α,β-unsaturated carbonyl compounds under solvent-free conditions at 55–60°C. The thio-Michael addition products were obtained in an excellent yield under optimised conditions. This methodology involving a metal-free as well as a metal scavenger catalyst has been found to be an alternative method for the thio-Michael addition reaction.

Keywords: SiliaBond® Thiourea – solvent-free Michael reaction – thioethers

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-011-0052-z

 

Chemical Papers 65 (5) 707–713 (2011)

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