Preparation of Polyfunctional Organozinc Halides by an InX3- and LiCl-Catalyzed Zinc Insertion to Aryl and Heteroaryl Iodides and Bromides
A catalytic system consisting of InCl3(3 mol %) and LiCl (30 mol %) allows a convenient preparation of polyfunctional arylzinc halides via the insertion of zinc powder to various aryl iodides in THF at 50 °C in up to 95 % yield. The use of a THF/DMPU (1:1) mixture shortens the reaction rates and allows the preparation of keto-substituted arylzinc reagents. In the presence of In(acac)3(3 mol %) and LiCl (150 mol %), the zinc insertion to various aryl and heteroaryl bromides proceeds smoothly (50 °C, 2–18 h). Alkyl bromides are also converted to the corresponding zinc reagents in the presence of In(acac)3(10 mol %) and LiCl (150 mol %) in 70–80 % yield.
Benischke, Andreas D.,Le Corre, Grégoire,Knochel, Paul
Synthesis of functionalized 2-arylpyridines from 2-halopyridines and various aryl halides via a nickel catalysis
An efficient nickel-catalyzed method devoted to the direct formation of functionalized 2-arylpyridines is described avoiding the prior preparation of organometallic species. Various functionalized 2-arylpyridines are obtained in moderate to excellent yields by a one-step chemical procedure from corresponding halides. The NiBr2(2,2′-bipyridine) complex appears to be an extremely suitable catalyst for the activation in the presence of manganese dust of aromatic halides and pyridyl halides functionalized by reactive groups. The versatility of this original process represents a simple alternative to most known methods using organometallic reagents.
Electrosynthesis of functionalized 2-arylpyridines from functionalized aryl and pyridine halides catalyzed by nickel bromide 2,2'-bipyridine complex
2-Arylpyridines substituted on aryl and/or on pyridine nuclei can be obtained in good to high yields in one step by electroreduction of mixtures of the corresponding aryl and pyridyl halides using the sacrificial iron anode process and a nickel 2,2'-bipyr
Gosmini, Corinne,Nédélec, Jean Yves,Périchon, Jacques
p. 5039 - 5042
(2007/10/03)
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