Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol.
Molecules
; 22(2)2017 Feb 20.
Article
en En
| MEDLINE
| ID: mdl-28230754
ABSTRACT
A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60 °C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Selenio
/
Alquinos
Idioma:
En
Revista:
Molecules
Asunto de la revista:
BIOLOGIA
Año:
2017
Tipo del documento:
Article
País de afiliación:
Brasil