Two Distinct Cyclizations of 2-Propenyl-1-ethynyl Benzenes with Aryldiazo Esters Using Au and Rh/Au Catalysts Respectively

Wagh Sachin Bhausaheb; Hsu Yu -Chen; Liu Rai-Shung

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Two Distinct Cyclizations of 2-Propenyl-1-ethynyl Benzenes with Aryldiazo Esters Using Au and Rh/Au Catalysts Respectively

机译：分别使用Au和Rh / Au催化剂的带有芳基重氮酯的2-丙烯基-1-乙炔基苯的两个不同的环化反应

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This work reports the development of two catalytic cyclizations of 2-propenyl-1-ethynylbenzenes with aryldiazo esters. Cationic gold catalyst produces 2-substituted 3-alkenyl-1H-indenes with substrates over a reasonable scope. Our mechanistic study suggests that arydiazo esters attack at the cyclopropyl moieties of gold carbene intermediates, followed by skeletal rearrangement of resulting intermediates. In the presence of Rh-2(esp)(2) additive, the same gold catalyst alters the chemoselectivity of these reactants to afford tetrahydro-1H-cyclopropa[b]naphthalenes with excellent stereoselectivity. Herein, Rh(II) catalyst catalyzed the reactions of the same 1,6-enynes with diazo species to form cyclopropenes initially, and a cationic Au(I) catalyst allows their subsequent reactions with the tethered alkenes. Preferable E-selectivity and synergistic effects of Au/Rh catalysts are rationalized in a postulated mechanism.

机译：这项工作报告了2-丙烯基-1-乙炔基苯与芳基重氮酯的两个催化环化的发展。阳离子金催化剂可在合理范围内生成带有底物的2-取代的3-烯基-1H-茚。我们的机理研究表明，重氮基酯会攻击金卡宾中间体的环丙基部分，然后对所得中间体进行骨架重排。在存在Rh-2（esp）（2）添加剂的情况下，相同的金催化剂会改变这些反应物的化学选择性，从而提供具有优异立体选择性的四氢-1H-环丙烷[b]萘。在此，Rh（II）催化剂催化相同的1,6-炔烃与重氮物质的反应最初形成环丙烯，而阳离子Au（I）催化剂允许它们随后与链状烯烃反应。假定的机理使Au / Rh催化剂的优选的E-选择性和协同作用合理化。

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《ACS catalysis》 |2016年第10期|共7页
作者
Wagh Sachin Bhausaheb; Hsu Yu -Chen; Liu Rai-Shung;
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正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
gold and rhodium catalysis; 2-propenyl-1-ethynylbenzenes; cyclopropanation; 1H-indenes; tetrahydro-1H-cyclopropabnaphthalenes;

机译：金和铑催化;2-丙烯基-1-乙炔基苯;环丙烷化;1H-茚;四氢-1H-环丙烷[b]萘;

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1. Two Distinct Cyclizations of 2-Propenyl-1-ethynyl Benzenes with Aryldiazo Esters Using Au and Rh/Au Catalysts Respectively [J] . Wagh Sachin Bhausaheb, Hsu Yu -Chen, Liu Rai-Shung ACS catalysis . 2016,第10期

机译：分别使用Au和Rh / Au催化剂的带有芳基重氮酯的2-丙烯基-1-乙炔基苯的两个不同的环化反应
2. Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole -Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction [J] . Nalivela Kumara Swamy, Rudolph Matthias, Baeissa Elham S., Advanced synthesis & catalysis . 2018,第11期

机译：序贯AU / Cu催化：通过分子内环化/分子化酰胺反应的两种催化剂单罐方案用于致密化羟基羟基酯的映选择性合成
3. Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole -Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction [J] . Nalivela Kumara Swamy, Rudolph Matthias, Baeissa Elham S., Advanced synthesis & catalysis . 2018,第11期

机译：序贯AU / Cu催化：通过分子内环化/分子化酰胺反应的两种催化剂单罐方案用于致密化羟基羟基酯的映选择性合成
4. 3D ORDERED MESOPOROUS Au/β-MnO2: HIGH-PERFORMANCE CATALYSTS FOR THE CATALYTIC OXIDATION OF BENZENE AND CARBON MONOXIDE [C] . Qing Ye, Jiansheng Zhao, Donghui Li, 6th international conference on environmental catalysis : Abstract book . 2010

机译：3D有序介孔Au /β-MnO2：用于苯和一氧化碳催化氧化的高性能催化剂
5. Investigation of Oxidized Carbon Supported Au Catalysts Synthesized Via Strong Electrostatic Adsorption of Au(en)2Cl3 for the Hydrochlorination of Acetylene to Vinyl Chloride Monomer [D] . ?Noble, Sean Reginald 2020

机译：通过强大的静电吸附于Au（Zh）2Cl3的乙炔氢氯化对氯乙烯单体的乙酰氯化氢氯化的氧化碳负载的Au催化剂的研究
6. Interfacial nanodroplets guided construction of hierarchical Au Au-Pt and Au-Pd particles as excellent catalysts [O] . Aijing Ma, Jie Xu, Xuehua Zhang, -1

机译：界面纳米液滴指导分层AuAu-Pt和Au-Pd颗粒作为优良催化剂的构建
7. Two Distinct Cyclizations of 2Propenyl-1-ethynyl Benzenes with Aryldiazo Esters Using Au and Rh/Au Catalysts Respectively [O] . -1

机译：分别使用Au和Rh / Au催化剂与青硝基唑酯的2苯基-1-苯炔基的两个不同的环化。
8. Observation of Au + Au yields Au + Au + rho(0) and Au + Au yields Au(asterik) +Au(asterik) + rho(0) with STAR [R] . Klein, S. 2001

机译：观察au + au产生au + au + rho（0）和au + au产生au（星号）+ au（星号）+ rho（0）与sTaR

Two Distinct Cyclizations of 2-Propenyl-1-ethynyl Benzenes with Aryldiazo Esters Using Au and Rh/Au Catalysts Respectively

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