PhSeBr-Catalyzed Selective Addition of Thiols to alpha,beta-Unsaturated Carbonyl Compounds: Regioselective Synthesis of Thioacetals vs. beta-Mercapto Ketones

作者:Schneider Caroline C; Manarin Flavia; Panatieri Rodrigo B; Barros Olga S R; Zeni Gilson*
来源:Journal of the Brazilian Chemical Society, 2010, 21(11): 2088-2092.
DOI:10.1590/S0103-50532010001100009

摘要

We present herein results on the PhSeBr-catalyzed addition of thiols to alpha,beta-unsaturated carbonyl compounds under mild conditions to afford regioselectivily beta-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 degrees 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.

  • 出版日期2010