Preparation of (E)-(2-iodovinyl)benzene from benzyl bromide and diiodomethane [(E)-beta-styryl iodide]
Author(s)
Bull, JA
Mousseau, JJ
Charette, AB
Type
Journal Article
Abstract
The procedure above provides a high yielding one-pot synthesis of (E)-β-styryl iodide from benzyl bromide and diiodomethane. This facile homologative method forms the C-C bond and installs the E-stereochemistry. Alkylation of NaCHI2 with benzyl bromide, followed by an in situ elimination of HI from the gem-diiodide intermediate in the presence of excess base provides the (E)-β-styryl iodide with high stereoselective. This method has been demonstrated to provide excellent E-selectivities using benzyl bromides with a range of steric and electronic requirements. Related methods allow the use of sensitive substrates and the synthesis of E-styryl chlorides and bromides.
Date Issued
2010
Citation
Org Synth, 2010, 87, pp.170-177
Start Page
170
End Page
177
Journal / Book Title
Org Synth
Volume
87
Copyright Statement
© 2010 The Authors.
Description
04.09.12 KB. Published version ok to add to spiral, Adam told by author (J. Bull) that authors hold the copyright. Papers are freely available on publisher website.
Identifier
http://orgsyn.org/orgsyn/prep.asp?prep=v87p0170
Publisher URL