1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

Holly V. Adcock; Thomas Langer; Paul W. Davies

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1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

机译：1,2-N-迁移在亚甲基酰胺的1,1-碳烷氧基化的金催化的功能化茚的合成中

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Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C-N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.

机译：独特的α-半缩合醚金卡宾中间体可通过金催化的1,1-羰基烷氧基化策略获得，并通过高度选择性的1,2-N迁移而演化。骨骼的这种重排产生了官能化的茚基，并且同位素标记证实了酰胺基部分的罕见C-N键裂解。已经探讨了取代基对迁移的影响，并提出了一个模型来合理化观察到的选择性。

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《Chemistry: A European journal》 |2014年第24期|共5页
作者
Holly V. Adcock; Thomas Langer; Paul W. Davies;
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正文语种 eng
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carbenes; cycloisomerisation; gold; regioselectivity; ynamides;

机译：卡宾;环异构化;金;区域选择性;酰胺;

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1. 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides [J] . Holly V. Adcock, Thomas Langer, Paul W. Davies Chemistry: A European journal . 2014,第24期

机译：1,2-N-迁移在亚甲基酰胺的1,1-碳烷氧基化的金催化的功能化茚的合成中
2. Facile Synthesis of Alkyl 1-Oxo-3-phenyl-1H-indene-2-carboxylate through Palladium-catalyzed Carboalkoxylation from 2-Bromo-3-phenylinden-1-ones [J] . Eul Kgun Yum, Woul Seong Park, Se Hoan Kim Chemistry Letters . 2008,第10期

机译：通过2-溴-3-苯基茚满-1-酮的钯催化碳烷氧基化反应轻松合成1-氧代-3-苯基-1H-茚-2-羧酸烷基
3. Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel–Crafts reaction of arylidenecyclopropanes with acetals [J] . Itaru Nakamura, Michiru Kamada, Yoshinori Yamamoto Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2004,第14期

机译：lide催化的碳烷氧基化/亚芳基环丙烷与缩醛的弗里德-克来夫茨反应合成茚满
4. Simple and General Procedure for the Synthesis of Semi-Rigid Chelating Agents for Radiometal Complexation Studies and its Application to Semi-Rigid Functionalised Ligands (BCA) Synthesis [C] . A.Loussouarn, A.F.Chauvet International Conference on Rare Earths . 1999

机译：用于合成半刚性螯合剂的简单且通用方法，用于放射摩托络合研究及其在半刚性官能化配体（BCA）合成中的应用
5. I. Synthesis of chiral ynamides. II. Reactions involving chiral ynamides. [D] . Mulder, Jason Alan. 2004

机译：I.手性炔酰胺的合成。二。涉及手性乙酰胺的反应。
6. 12-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 11-Carboalkoxylation of Ynamides [O] . Holly V Adcock, Thomas Langer, Paul W Davies -1

机译：12-N-迁移在亚甲基酰胺的11-碳烷氧基化反应的金催化的功能化茚的合成中
7. 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides [O] . Holly V. Adcock, Thomas Langer, Paul W. Davies 2014

机译：在官能1,1-碳酸氧化物化的官能化茚结合的金色催化合成中的1,2-n-迁移
8. Results from a Oral (Gavage) 28-day Oral Toxicity Study (OECD Guideline 407) Test with 1H-Indene-Ar-Propanal, 2,3-Dihydro-1,1-Dimethyl-(9CI) in Rats. [R] . 2012

机译：口服（管饲）28天口服毒性研究（OECD指南407）的结果用1H-茚-ar-丙醛，2,3-二氢-1,1-二甲基 - （9CI）在大鼠中进行试验。

1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

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