Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols

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.

Automated summary

The nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols proceeds efficiently under mild conditions in the presence of zinc powder and MgCl2 to produce allylarenes in moderate to high yields. The reaction exhibits high regioselectivity and E/Z-selectivity, particularly when 1- or 3-arylallyl alcohols are used as substrates. Various functional groups and nitrogen-containing heterocycles are tolerated in the reaction.