The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, .alpha.,.beta.-unsaturated ketones, and allylic, aryl, and vinyl halides

TL;DR: In this paper, a range of highly functionalized organozinc compounds have been synthesized in the presence of Cu(I) salts, which can cross-couple with acid chlorides, conjugatively add to α, β-unsaturated ketones, and regioselectively undergo S N 2' substitution reactions with allylic halides.

Abstract: Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl 2 , readily undergoes oxidative addition to alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds in excellent yields. Significantly, the reaction will tolerate a spectrum of functional groups on the organic halides. Accordingly, this approach can now be used to prepare a wide variety of highly functionalized organozinc compounds. In the presence of Cu(I) salts, the organozinc compounds cross-couple with acid chlorides, conjugatively add to α,β-unsaturated ketones, and regioselectively undergo S N 2' substitution reactions with allylic halides. They also cross-couple with aryl or vinyl halides with Pd(O) catalysts