ニッケル触媒による塩化アリル、アルキン、ビニルシクロプロパンのドミノカップリング反応の開発

抄録

Mild Ni(0)-catalyzed transformation a ring opening process of cyclopropyl compounds having an unsaturated bond, such as vinylcyclopropanes (VCPs), has attracted considerable attention. We investigated the reaction of the Ni-catalyzed coupling of alkyne-tethered vinylcyclopropane and allyl chloride. The reaction would undergo a beta-carbon eliminations of cyclopropylcarbinylnickel intermediate, which is caused by the addition of allylnickel species to an alkyne moiety and the subsequent incorporation of the intramolecular VCP moiety, to afford coupling product.
As a result of investigating reaction condition, the reaction of yne-vinylcyclopropane with allyl chloride was carried out in the presence of 10 mol % Ni(cod)₂, 20 mol % PPh₃ and 200 mol % Zn powder in MeCN at room temperature, to give the corresponding product in 55% yield.

fig.1