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Updated: Oct 14, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols
Hang Yu1, Zhong-Xia Wang1,2
1CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China. zxwang@ustc.edu.cn.
Abstract:
Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols proceeds readily under mild conditions in the presence of zinc powder and MgCl2 to produce allylarenes in 25-92% yields. The reaction shows high regioselectivity and E/Z-selectivity, giving linear allylation products with an E configurated double bond when 1- or 3-arylallyl alcohols were used as the substrates. Functional groups including F, CF3, COOEt, NMe2, OMe, SiMe3, OH and vinyl groups as well as nitrogen-containing heterocycles were tolerated.
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Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.