Journal
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
Volume 18, Issue 5, Pages 943-950Publisher
SOC BRASILEIRA QUIMICA
DOI: 10.1590/S0103-50532007000500011
Keywords
microwave irradiation; solvent-free reaction; beta-phenylchalcogeno esters; beta-phenylchalcogeno ketones; beta-phenylchalcogeno nitrites
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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.
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