Direct Copper(I) Iodide Dimethyl Sulfide Catalyzed Conjugate Addition of Alkenyl Groups from Vinylzirconocene Reagents

Abstract

[reaction: see text] CuI.0.75DMS complex is an excellent catalyst for the direct conjugate addition of alkenyl groups from vinylzirconocene reagents to alpha,beta-unsaturated aldehydes and ketones. The presence of the catalyst with an alkenylzirconocene, at +40 degrees C in THF, circumvents the need for making discrete alkenylcopper reagents. The catalyst is superior in terms of product yields and alkene flexibility in comparison to other copper(I) sources as well as the nickel(II)-catalyzed conjugate addition. This simple one-pot procedure shows that only 1 equiv of the vinylzirconocene is needed.