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Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide Salts and Alkyl Halides as Convenient HX Surrogates

机译:钯催化的1,6-炔烃的氢卤代反应:卤化氢盐和烷基卤化物作为方便的HX替代物

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摘要

Difficulties associated with handling H_2 and CO in metal-catalyzed processes have led to the development of chemical surrogates to these species. Despite many successful examples using this strategy, the application of convenient hydrogen halide (HX) surrogates in catalysis has lagged behind considerably. We now report the use of ammonium halides as HX surrogates to accomplish a Pd-catalyzed hydrohalogenation of enynes. These safe and practical salts avoid many drawbacks associated with traditional HX sources including toxicity and corrosiveness. Experimental and computational studies support a reaction mechanism involving a crucial E-to-Z vinyl-Pd isomerization and a carbon-halogen bond-forming reductive elimination. Furthermore, rare examples of C(sp~3)-Br and -Cl reductive elimination from Pd(II) as well as transfer hydroiodination using 1-iodobutane as an alternate HI surrogate are also presented.
机译:在金属催化过程中与处理H_2和CO有关的困难导致了针对这些物种的化学替代物的发展。尽管使用该策略获得了许多成功的实例,但在催化中使用方便的卤化氢(HX)替代物却远远落后。我们现在报告使用卤化铵作为HX替代物来完成Pd催化的炔烃氢化卤代反应。这些安全实用的盐避免了与传统HX来源相关的许多缺点,包括毒性和腐蚀性。实验和计算研究支持涉及关键的E-Z乙烯基Pd异构化和形成碳-卤素键的还原消除反应机理。此外,还提供了从Pd(II)还原C(sp〜3)-Br和-Cl的罕见例子,以及使用1-碘丁烷作为替代HI替代物进行转移加氢碘化的例子。

著录项

  • 来源
    《Journal of the American Chemical Society》 |2017年第9期|3546-3557|共12页
  • 作者单位

    Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada;

    Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada;

    Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada;

    Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada;

    Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Geneva, Switzerland;

    Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 eng
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  • 入库时间 2022-08-18 03:07:56

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