info:eu-repo/semantics/article
Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
Fecha
2015-12-09Registro en:
Heredia, Adrián Alberto; Peñeñory, Alicia Beatriz; Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions; Royal Society of Chemistry; RSC Advances; 5; 9-12-2015; 105699-105706
2046-2069
CONICET Digital
CONICET
Autor
Heredia, Adrián Alberto
Peñeñory, Alicia Beatriz
Resumen
A simple procedure for the synthesis of alkyl styryl selenides was developed. This methodology involves the in situ generation of selenolate anions by a one-pot and three-step protocol where a nucleophilic substitution between KSeCN and alkyl halides affords the corresponding alkyl selenocyanate in the first step, giving dialkyl diselenide by a further K3PO4-assisted reaction. Subsequent reduction yields the alkyl selenolate anions which react with substituted (E,Z)-β-styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require a catalyst, proceeds under an air atmosphere and within a short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.