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Sociedade Brasileira de Química, SBQ, Journal of the Brazilian Chemical Society, 5(18), p. 943-950, 2007

DOI: 10.1590/s0103-50532007000500011

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Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

A simple, clean and efficient solvent-free protocol was developed for hydrochalcogenation of alkynes containing a Michael acceptor (ester, ketone and nitrile) with phenylchalcogenolate anions generated in situ from the respective diphenyl dichalcogenide (Se, Te, S), using alumina supported sodium borohydride. This efficient and improved method is general and furnishes the respective (Z)-beta-phenylchalcogeno-alpha,beta-unsaturated esters, ketones and nitriles, in good yield and higher selectivity, compared with those that use organic solvent and inert atmosphere. The use of microwave (MW) irradiation facilitates the procedure and accelerates the reaction.