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Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents.

ABSTRACT: In this review we summarize the most important procedures for the preparation of functionalized organzinc and organomagnesium reagents. In addition, new methods for the preparation of polyfunctional aryl- and heteroaryl zinc- and magnesium compounds, as well as new Pd-catalyzed cross-coupling reactions, are reported herein. Experimental details are given for the most important reactions in the Supporting Information File 1 of this article.

SUBMITTER: Knochel P

PROVIDER: S-EPMC3182436 | biostudies-other | 2011

REPOSITORIES: biostudies-other

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Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents.

Knochel Paul P Schade Matthias A MA Bernhardt Sebastian S Manolikakes Georg G Metzger Albrecht A Piller Fabian M FM Rohbogner Christoph J CJ Mosrin Marc M

Beilstein journal of organic chemistry 20110913

In this review we summarize the most important procedures for the preparation of functionalized organzinc and organomagnesium reagents. In addition, new methods for the preparation of polyfunctional aryl- and heteroaryl zinc- and magnesium compounds, as well as new Pd-catalyzed cross-coupling reactions, are reported herein. Experimental details are given for the most important reactions in the Supporting Information File 1 of this article. ...[more]

PMID: 21977211

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Project description:Reactions of three magnesium(i) dimers, [{(ArNacnac)Mg-}2] (ArNacnac = [(ArNCMe)2CH]-; Ar = xylyl (Xyl), mesityl (Mes) or 2,6-diethylphenyl (Dep)), with either 1,1-diphenylethylene (DPE), ?-methylstyrene (MS), trans-stilbene (TS) or diphenylacetylene (DPA) led to the 1,2-addition of the Mg-Mg bond across the substrate, giving rise to the 1,2-dimagnesioethanes, [{(XylNacnac)Mg}2(?-DPE)], [{(DepNacnac)Mg}2(?-MS)], [{(ArNacnac)Mg}2(?-TS)] (Ar = Mes or Dep); and a 1,2-dimagnesioethene, [{(MesNacnac)Mg}2(?-DPA)]. The reactions involving the 1,1-substituted alkenes are shown to be readily redox reversible, in that the reaction products are in equilibrium with a significant proportion of the starting materials at room temperature. Variable temperature NMR spectroscopy and a van't Hoff analysis point to low kinetic barriers to these weakly exergonic reactions. [{(MesNacnac)Mg}2(?-DPE)] and [{(MesNacnac)Mg}2(?-DPA)] behave as 1,2-di-Grignard reagents in their reactions with very bulky amido-zinc bromides, yielding the first examples of a 1,2-dizincioethane, [(L*Zn)2(?-DPE)] (L* = -N(Ar*)(SiPri 3); Ar* = C6H2Me{C(H)Ph2}2-4,2,6), and a 1,2-dizincioethene, [(TBoLZn)2(?-DPA)] (TBoL = -N(SiMe3){B(DipNCH)2}, Dip = 2,6-diisopropylphenyl), respectively. Divergent reactivity is shown for [{(MesNacnac)Mg}2(?-DPE)], which behaves as a two-electron reducing agent when treated with amido-cadmium and amido-magnesium halide precursors, yielding the cadmium(i) and magnesium(i) dimers, [PhBoLCdCdPhBoL] (PhBoL = -N(SiPh3){B(DipNCH)2}) and [L†MgMgL†] (L† = -N(Ar†)(SiMe3); Ar† = C6H2Pri{C(H)Ph2}2-4,2,6), respectively. A further class of reactivity for [{(MesNacnac)Mg}2(?-DPE)] derives from its reaction with the bulky amido-germanium chloride, L*GeCl, which gives a magnesio-germane, presumably via intramolecular C-H activation of a highly reactive magnesiogermylene intermediate, [:Ge(L*){Mg(MesNacnac)}]. [{(MesNacnac)Mg}2(?-DPE)] can be considered as acting as a two-electron reducing, magnesium transfer reagent in this reaction.

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Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents.

Publications

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents.

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