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FeX 3 ‐Promoted Intermolecular Addition of Benzylic Alcohols to Aromatic Alkynes: A Mild and Efficient Strategy for the Synthesis of Alkenyl Halides
Author(s) -
Ren Kai,
Wang Min,
Wang Lei
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901020
Subject(s) - chemistry , halide , bromide , intermolecular force , stereoselectivity , organic chemistry , medicinal chemistry , chloride , catalysis , molecule
A convenient, effective, mild and simple strategy has been developed for the synthesis of alkenyl halides by the intermolecular addition of benzylic alcohols to aromatic alkynes. The reactions were carried out in the presence of iron(III) bromide or chloride in 1,2‐dibromoethane without additives in air at room temperature. Alkenyl bromides and chlorides were obtained with high regio‐ and stereoselectivity ( E / Z up to 99:1) in good‐to‐excellent yields in 0.5–1 h under mild reaction conditions.