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Issue 128, 2015
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Stereoselective synthesis of alkyl styryl selenides in one-pot: a straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions

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Abstract

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.

Graphical abstract: Stereoselective synthesis of alkyl styryl selenides in one-pot: a straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions

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Article information


Submitted
08 Oct 2015
Accepted
07 Dec 2015
First published
09 Dec 2015

RSC Adv., 2015,5, 105699-105706
Article type
Paper
Author version available

Stereoselective synthesis of alkyl styryl selenides in one-pot: a straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions

A. A. Heredia and A. B. Peñéñory, RSC Adv., 2015, 5, 105699
DOI: 10.1039/C5RA20883A

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