Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp(2))-C(sp(3)) Bonds: Scope and Mechanism

Phapale VB; Guisan-Ceinos M; Bunuel E; Cardenas DJ

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Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp(2))-C(sp(3)) Bonds: Scope and Mechanism

机译：镍催化的烷基卤化锌交叉偶联形成C（sp（2））-C（sp（3））键：范围和机理

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Optimal conditions for a general Ni-catalysed Negishi cross-coupling of alkyl zinc halides with aryl, heteroaryl and alkenyl halides have been determined. These conditions allow the reaction to take place smoothly, with low catalyst loading, and in the presence of a wide variety of functional groups to afford products in good yields at room temperature. DFT studies on the mechanism support the occurrence of a catalytic cycle involving transmetalation of the alkyl zinc halide to Ni-I followed by oxidative addition of the haloarene and C-C reductive elimination.

机译：已经确定了烷基镍卤化物与芳基，杂芳基和烯基卤化物的一般的Ni催化的Negishi交叉偶联的最佳条件。这些条件使反应能够在低催化剂负载下并且在多种官能团的存在下平稳地进行，从而在室温下以高收率提供产物。关于该机理的DFT研究支持了催化循环的发生，该催化循环包括将烷基卤化锌转金属为Ni-I，然后氧化卤代芳烃并进行C-C还原消除。

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《Chemistry: A European journal》 |2009年第46期|共8页
作者
Phapale VB; Guisan-Ceinos M; Bunuel E; Cardenas DJ;
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正文语种 eng
中图分类应用化学;
关键词
C-C coupling; densityfunctional calculations; homogeneous catalysis; nickel; radical reactions;

机译：碳-碳耦合;密度泛函计算;均相催化;镍;自由基反应;

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1. Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp2)C(sp3) Bonds: Scope and Mechanism [J] . Vilas B. Phapale Manuel Guisaacute, n-Ceinos Elena Buntilde, uel Prof. Dr. Diego J. Caacute, Chemistry - A European Journal . 2010,第11期

机译：镍催化烷基卤化锌交叉偶联形成C（sp 2 ）C（sp 3 ）键的范围和机理
2. On the Nature of C(sp~3)-C(sp~2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides [J] . Mingbin Yuan, Zhihui Song, Shorouk O. Badir, Journal of the American Chemical Society . 2020,第15期

机译：镍催化的叔自由基交叉偶联中C（sp〜3）-C（sp〜2）键形成的性质：以烷基自由基和芳基卤化物的Ni / Photoredox催化交叉偶联为例
3. Ni-Catalyzed Cascade Formation of C(sp3)-C(sp3) Bonds by Cyclization and Cross-Coupling Reactions of Iodoalkanes with Alkyl Zinc Halides [J] . Vilas B.Phapale, Elena Bunuel, Miguel Garcia-Iglesias Angewandte Chemie . 2007,第46期

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4. Ni/Co-Catalyzed C(sp~3)-C(sp~3) Cross-Coupling Using Alkyl Tosylates as Radical Sources [C] . Takuya Michiyuki, Itaru Osaka, Kimihiro Komeyama 日本化学会春季年会講演予稿集 . 2018

机译：Ni /助催化的C（SP〜3）-C（SP〜3）使用烷基甲磺酸盐作为自由基来源的交叉偶联
5. Palladium-mediated carbon-carbon bond formation: Methodology and mechanism. Part I: Palladium-catalyzed alpha-arylation of aryl nitromethanes, phosphonoacetates, and phosphine oxides. Part II: Mechanistic study of the palladium-mediated chemoselective activation of C(sp3)-H bonds. [D] . VanGelder, Kelsey Faith. 2016

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6. Metallaphotoredox-Catalyzed sp3–sp3 Cross-Coupling of Carboxylic Acids with Alkyl Halides [O] . Craig P. Johnston, Russell T. Smith, Simon Allmendinger, -1

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7. Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp2)C(sp3) Bonds: Scope and Mechanism [O] . Vilas B. Phapale, Manuel Guisán-Ceinos, Elena Buñuel, 2010

机译：烷基锌卤化物的镍催化的交叉偶联用于形成C（SP2）C（SP3）键：范围和机制

Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp(2))-C(sp(3)) Bonds: Scope and Mechanism

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