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

• Autor(a) principal: Schneider,Caroline C
• Data de Publicação: 2010
• Outros Autores: Manarin,Flávia, Panatieri,Rodrigo B, Barros,Olga S. R, Zeni,Gilson
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100009
• topic: thioacetals; β-mercapto ketones; chalcogenides

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 ºC, 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.