Gold-Catalyzed Formal Dehydro-Diels-Alder Reactions of Ene-Ynamide Derivatives Bearing Terminal Alkyne Chains: Scope and Mechanistic Studies

被引:47
作者
Zhao, Qing [1 ,2 ]
Leon Rayo, David Fabian [3 ]
Campeau, Dominic [3 ]
Daenen, Martin [3 ]
Gagosz, Fabien [1 ,2 ,3 ]
机构
[1] Ecole Polytech, UMR 7652, Dept Chim, F-91128 Palaiseau, France
[2] Ecole Polytech, CNRS 7653, F-91128 Palaiseau, France
[3] Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
cycloaddition; gold; heterocycles; reaction kinetics; reaction mechanisms; C-H INSERTION; CYCLIZATION; VINYLIDENE; GENERATION; ACETYLIDES; ACCESS; CYCLOADDITION; CARBAZOLES; ACTIVATION; COMPLEXES;
D O I
10.1002/anie.201807136
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new protocol for the synthesis of a variety of N-containing aromatic heterocycles by a formal gold-catalyzed dehydro-Diels-Alder reaction of ynamide derivatives has been developed. Deuterium-labeling experiments and kinetic studies support the involvement of a dual gold catalysis mechanism in which a gold acetylide moiety adds onto an aurated keteneiminium.
引用
收藏
页码:13603 / 13607
页数:5
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