3 years ago

Preparation of Organozinc Reagents via Catalyst Controlled Three-Component Coupling between Alkyne, Iodoarene, and Bis(iodozincio)methane

Preparation of Organozinc Reagents via Catalyst Controlled Three-Component Coupling between Alkyne, Iodoarene, and Bis(iodozincio)methane
Yukako Shimada, Zenichi Ikeda, Seijiro Matsubara
Three-component coupling between an alkyne, iodoarene, and bis(iodozincio)methane yields allylic zinc with a tetrasubstituted alkene moiety in the presence of a nickel catalyst. The reaction proceeds via aryl nickelation of the alkyne and subsequent cross-coupling with bis(iodozincio)methane. Meanwhile, the same combination in the presence of a palladium and cobalt catalyst gives tetrasubstituted alkenylzinc. The reaction proceeds via a palladium-catalyzed cross-coupling of iodoarene with bis(iodozincio)methane followed by a cobalt-catalyzed benzylzincation of alkyne.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00917

DOI: 10.1021/acs.orglett.7b00917

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