Journal
RSC ADVANCES
Volume 5, Issue 128, Pages 105699-105706Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra20883a
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Funding
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET)
- Fondo de Ciencia y Tecnologia (FONCYT), Argentina
- CONICET
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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)-beta-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.
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