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

Universidade Federal de Góias, Goiania, Brazil¹  Panatieri, Rodrigo B¹  Universidade Federal de Uberlândia, Ituiutaba, Brazil¹  UFSM, Santa Maria, Brazil¹  Manarin, Flávia¹  Schneider, Caroline C¹  Barros, Olga S. R¹  Zeni, Gilson¹ 

关键词: thioacetals;    β-mercapto ketones;    chalcogenides;   

DOI  :  10.1590/S0103-50532010001100009

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

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.

【 授权许可】

Unknown