Nickel-Catalyzed Homocoupling of (Z)-β-Iodoenol Esters: Stereoselective Access to (Z,Z)-Buta-1,3-diene-1,4-diyl Diesters

Dedicated to Prof. Pablo Espinet on the occasion of his 70^th birthday

Abstract

A straightforward and broad-scope procedure to obtain symmetrically substituted buta-1,3-diene-1,4-diyl diesters, based on the homocoupling of the corresponding (Z)-β-iodoenol esters, is presented. It involves the use of a catalytic system composed of [NiCl₂(PPh₃)₂] (10 mol%), NaI (10 mol%), and excess of Zn dust. The reactions proceed in THF at room temperature with exquisite preservation of the stereochemistry of the C=C bond of the starting iodoolefins, thus leading to the final dienes as the corresponding Z,Z-stereoisomers exclusively.

Key words

homocoupling reactions - nickel - iodoalkenes - buta-1,3-dienes - enol esters - diesters

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