Stereoselective Synthesis of Alkyl Styryl Selenides in One-Pot: A Straightforward Approach by in situ Dialkyl Diselenide Formation under Transition Metal-Free Conditions

ADRIAN HEREDIA; ALICIA B. PEÑÉÑORY

RSC Advances

Royal Society of Chemistry

Año: 2015 vol. 5 p. 105699 - 105706

2046-2069

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)--styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require catalyst, proceeds under air atmosphere and within short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.