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首页> 外文期刊>RSC Advances >Ag2O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
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Ag2O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins

机译：Ag2O纳米粒子催化的基质控制区域：直接进入3- ylidenephaliders和Isocoumarins

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摘要

Herein, we disclose the first example of an efficient, silver oxide nanoparticle-catalyzed, direct regioselective synthesis of 3-ylidenephthalides 11-16 and isocoumarins 17-20via sonogashira type coupling followed by substrate-controlled 5-exo-dig or 6-endo-dig cyclization reaction, respectively. This one pot coupling involves reaction of substituted 2-halobenzoic acid with meta/para-substituted and ortho-substituted terminal alkynes, which proceeded in a regioselective manner resulting in the formation of 3-ylidenephthalides or isocoumarins, respectively, in excellent yields (up to 95%) with complete Z-selectivity. This protocol features relatively broad substrate scope, mild conditions, operational simplicity, and is favourable with aromatic/alicyclic terminal alkynes. The competition experiments and gram-scale synthesis further highlight the importance and versatility of the methodology. The proposed mechanistic pathways illustrate that the regioselectivity is substantially being controlled by the substituent(s) present on the acetylenic phenyl ring.
机译：在本文中，我们公开了一种高效，银氧化物纳米颗粒催化的，区域选择性直接3- ylidenephthalides 11-16合成的第一个例子和异香豆素17-20via的Sonogashira型偶联，随后基板控制5 - 外掏或6-内 - 挖环化反应，分别。此一个锅煮耦合涉及取代的2-卤代酸与间/对 - 取代的和邻 - 取代的末端炔烃，其在导致3- ylidenephthalides或异香豆素，形成了区域选择性的方式分别进行，以优良产率的反应（最高95％）与完全Z-选择性。该协议设有相对宽的底物范围，在温和的条件，操作简便性，并与芳族化合物/脂环族末端炔有利。竞争实验和克级合成进一步突出方法论的重要性和多功能性。所提出的机制途径示出了区域选择性基本上由取代基（一个或多个）本炔苯基环上的控制。

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  • 来源
    《RSC Advances》 |2018年第41期|共11页
  • 作者

    Chaudhary Sandeep; Shyamlal Bharti Rajesh K.; Yadav Lalit; Tiwari Mohit K.; Kumar Krishan;

  • 作者单位

    Malaviya Natl Inst Technol Jaipur Lab Organ &

    Med Chem Dept Chem Jawaharlal Nehru Marg Jaipur 302017 Rajasthan India;

    Malaviya Natl Inst Technol Jaipur Lab Organ &

    Med Chem Dept Chem Jawaharlal Nehru Marg Jaipur 302017 Rajasthan India;

    Malaviya Natl Inst Technol Jaipur Lab Organ &

    Med Chem Dept Chem Jawaharlal Nehru Marg Jaipur 302017 Rajasthan India;

    Malaviya Natl Inst Technol Jaipur Lab Organ &

    Med Chem Dept Chem Jawaharlal Nehru Marg Jaipur 302017 Rajasthan India;

    Malaviya Natl Inst Technol Jaipur Lab Organ &

    Med Chem Dept Chem Jawaharlal Nehru Marg Jaipur 302017 Rajasthan India;

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  • 正文语种 eng
  • 中图分类 化学;
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