Intramolecular hydroarylation of alkynes catalyzed by platinum or gold: Mechanism and endo selectivity

Nevado C; Echavarren AM

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Intramolecular hydroarylation of alkynes catalyzed by platinum or gold: Mechanism and endo selectivity

机译：铂或金催化炔烃的分子内加氢芳基化：机理和内选择性

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The cyclization of differently substituted aryl alkynes with Pt-II or Au-I catalysts proceeds by endo-dig pathways. When Ag-I was used to generate reactive cationic Au-I catalysts, 2H-chromenes dimerize to form cyclobutane derivatives by a Ag-I-catalyzed process. A DFT study on the cyclization mechanism shows a kinetic and thermodynamic preference for 6-endo-dig versus 5-exo-dig cyclizations in Pt-II-catalyzed processes. Calculations indicate that although Friedel-Crafts and the cyclopropanation processes via metal cyclopropyl carbenes show very similar activation energies, platinum cyclopropyl carbenes are the stationary points with the lowest energy.

机译：Pt-II或Au-I催化剂对不同取代的芳基炔烃的环化作用是通过内挖途径进行的。当使用Ag-1生成反应性阳离子Au-1催化剂时，2H-色烯通过Ag-1催化过程二聚形成环丁烷衍生物。 DFT对环化机理的研究表明，在Pt-II催化的过程中，动力学上和热力学上偏爱6-内切和5-外切。计算表明，尽管Friedel-Crafts和通过金属环丙基卡宾进行的环丙烷化过程显示出非常相似的活化能，但铂环丙基卡宾是能量最低的固定点。

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《Chemistry: A European journal》 |2005年第10期|共10页
作者
Nevado C; Echavarren AM;
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正文语种 eng
中图分类化学;
关键词
alkynes; cyclization; density functional calculations; gold; platinum; C-H BONDS; CYCLOISOMERIZATION REACTIONS; VINYLIDENE COMPLEXES; TRANSITION-METALS; AROMATIC ENYNES; TRIPLE BONDS; ENOL ETHERS; CYCLIZATION; ARENES; COUMARINS;

机译：炔烃;环化;密度泛函计算;金;铂;C-H键;环异构化反应;亚乙烯基络合物;过渡金属;芳族烯基;三键;烯醇醚;环化;芳烃;COUMARINS;

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1. Intramolecular hydroarylation of alkynes catalyzed by platinum or gold: Mechanism and endo selectivity [J] . Nevado C, Echavarren AM Chemistry: A European journal . 2005,第10期

机译：铂或金催化炔烃的分子内加氢芳基化：机理和内选择性
2. The mechanism and regioselectivity of gold(Ⅰ) or platinum(Ⅱ) catalyzed intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones [J] . Ran Fang, Xiaoxiao Wei, Lizi Yang Organic & biomolecular chemistry . 2014,第42期

机译：金（Ⅰ）或铂（Ⅱ）催化分子内加氢芳基化反应生成吡咯并吡啶并酮和吡咯并ze庚酮类化合物的机理和区域选择性
3. Total Synthesis of (+/-)-2-Debromohymenin via Gold-Catalyzed Intramolecular Alkyne Hydroarylation [J] . Singh Ravi P., Bhandari Manojkumar R., Torres Fatima M., Organic letters . 2020,第9期

机译：通过金催化的分子内炔烃水红液总合成（+/-） - 2-德布洛昔核苷酸
4. Intramolecular Reactions of Alkynes with Alkenes Catalyzed by Platinum and Gold [C] . Antonio M. Echavarren, Cristina Nevado, Cristina Nieto-Oberhuber, NATO Advanced Study Institute on New Methodologies and Techniques for a Sustainable Organic Chemistry: Sustainable Development in a Secure Environment Certosa di Pontignano . 2008

机译：铂和金催化烯烃的分子内反应
5. I. Platinum, gold, and ruthenium-catalyzed reactions of multi-ynes: Reactivity and selectivity. II. Synthetic studies on natural products: 3R,9R,10R-panaxytriol and (-)-dactylolide. [D] . Cho, Eun Jin. 2008

机译：I.铂，金和钌催化的多炔反应：反应性和选择性。二。天然产物的合成研究：3R，9R，10R-人参三醇和（-）-二环己内酯。
6. Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones [O] . Xiaochen Du, Jianjun Huang, Anton A Nechaev, 2018

机译：金催化的Ugi后炔烃加氢芳基化反应合成2-喹诺酮
7. Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes [O] . -1

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Intramolecular hydroarylation of alkynes catalyzed by platinum or gold: Mechanism and endo selectivity

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