Formation of Oxazoles from Elusive Gold(I) alpha-Oxocarbenes: A Mechanistic Study

Schulz Jiri; Jasik Juraj; Gray Andrew; Roithova Jana

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Formation of Oxazoles from Elusive Gold(I) alpha-Oxocarbenes: A Mechanistic Study

机译：由难以捉摸的金（I）α-氧碳烯形成恶唑的机理研究

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The gold(I) catalyzed reaction between phenylacetylene, pyridine N-oxide and acetonitrile leading, via a putative gold-alpha-oxocarbene intermediate, towards an oxazole product has been investigated. A novel mass spectrometric method called "delayed reactant labeling" is used to track consecutive and parallel reactions. It clearly shows that the intramolecular formation of a pyridine adduct of gold-alpha-oxo-carbene is in competition with the formation of the oxazole product. The reaction mechanism most probably corresponds to competition between acetonitrile and pyridine in an almost barrierless reaction with putative gold-alpha-oxocarbene within the solvent cage. The detected ionic species have been characterized by helium tagging infrared photo-dissociation spectroscopy.

机译：研究了苯乙炔，吡啶N-氧化物和乙腈之间的金（I）催化反应，该反应通过推定的金-α-氧代碳烯中间体导致生成恶唑产物。一种称为“延迟反应物标记”的新型质谱方法用于跟踪连续和平行的反应。清楚地表明，金-α-氧代卡宾的吡啶加合物的分子内形成与恶唑产物的形成竞争。该反应机理很可能与乙腈和吡啶在溶剂笼中与假定的金-α-氧卡宾几乎无障碍反应中的竞争相对应。通过氦标记红外光解离光谱法对检测到的离子种类进行了表征。

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《Chemistry: A European journal》 |2016年第28期|共8页
作者
Schulz Jiri; Jasik Juraj; Gray Andrew; Roithova Jana;
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正文语种 eng
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carbenes; gold catalysis; mass spectrometry; reaction intermediates; reaction mechanism;

机译：卡宾;金催化;质谱;反应中间体;反应机理;

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1. Formation of Oxazoles from Elusive Gold(I) alpha-Oxocarbenes: A Mechanistic Study [J] . Schulz Jiri, Jasik Juraj, Gray Andrew, Chemistry: A European journal . 2016,第28期

机译：由难以捉摸的金（I）α-氧碳烯形成恶唑的机理研究
2. Gold Catalysis:Mild Conditions for the Synthesis of Oxazoles from N-Propargylcarboxamides and Mechanistic Aspects [J] . A.Stephen K.Hashmi, Jan P.Weyrauch, Wolfgang Frey Organic letters . 2004,第23期

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3. [3,3]-Sigmatropic Rearrangement versus Carbene Formation in Gold-Catalyzed Transformations of Alkynyl Aryl Sulfoxides: Mechanistic Studies and Expanded Reaction Scope [J] . Biao Lu, Yuxue Li, Youliang Wang, Journal of the American Chemical Society . 2013,第23期

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Formation of Oxazoles from Elusive Gold(I) alpha-Oxocarbenes: A Mechanistic Study

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