PhSeBr-catalyzed selective addition of thiols to α,β- unsaturated carbonyl compounds: regioselective synthesis of thioacetals vs. β-mercapto ketones

Resumo

We present herein results on the PhSeBr-catalyzed addition of thiols to α,β-unsaturated carbonyl compounds under mild conditions to afford regioselectivily β-mercapto ketones or thioacetals in high yields and selectivity. The reaction was highly controlled by the temperature in which, the 1,4-addition products were obtained when the temperature was –20 °C, conversely when the reaction was carried out at reflux, the thioacetals were obtained as a sole product. The developed protocol stands a wide range of functional groups, in which alkyl, benzyl and aryl with neutral, electron deficient and electron rich substituents on the aromatic ring.

Descrição

Palavras-chave

Thioacetals, β-mercapto ketones, Chalcogenides

Citação

SCHNEIDER , Caroline C. et al. PhSeBr-catalyzed selective addition of thiols to α,β- unsaturated carbonyl compounds: regioselective synthesis of thioacetals vs. β-mercapto ketones. Journal of the Brazilian Chemical Society, Campinas, v. 21, n. 11, p. 2088-2092, July 2010.