131379-22-1Relevant academic research and scientific papers
Air-stable solid aryl and heteroaryl organozinc pivalates: Syntheses and applications in organic synthesis
Manolikakes, Sophia M.,Ellwart, Mario,Stathakis, Christos I.,Knochel, Paul
, p. 12289 - 12297 (2015/03/31)
A wide range of air-stable, solid, polyfunctional aryl and heteroarylzinc pivalates were efficiently prepared by either magnesium insertion or Hal/Mg exchange followed by transmetalation with Zn(OPiv)2 (OPiv=pivalate). By reducing the amount of
Sterically hindered lithium dialkylcuprates for the generation of highly functionalized mixed cuprates through a halogen-copper exchange
Piazza, Claudia,Knochel, Paul
, p. 3263 - 3265 (2007/10/03)
Even aldehyde and ketone functions are tolerated in mixed organocuprates prepared by copper-halogen exchange using (Me3CCH2)2CuLi (Neopent2CuLi) or (PhMe2CCH2)2CuLi (Neophyl2CuLi). The steric hindrance of the neopentyl and neophyl groups is essential to ensure the chemoselectivity of the reaction (see scheme), and therefore allows a general preparation of polyfunctionalized organocuprates.
Highly reactive forms of zinc and reagents thereof
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, (2008/06/13)
A novel zerovalent zinc species and an organozinc reagent are disclosed. The zerovalent zinc species is directly produced by reaction of a reducing agent on a zinc salt, preferably Zn(CN)2. The organozinc reagent results from the reaction of the zerovalent zinc species and an organic compound having one or more stable anionic leaving groups. These organozinc reagents include a wide spectrum of functional groups in the organic radical, and are useful in a variety of reactions schemes.
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, α,β-Unsaturated Ketones, and Allylic, Aryl, and Vinyl Halides
Zhu, Lishan,Wehmeyer, Richard M.,Rieke, Reuben D.
, p. 1445 - 1453 (2007/10/02)
Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl2, 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 SN2' substitution reactions with allylic halides.They also cross-couple with aryl or vinyl halides with Pd(0) catalysts.
