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

被引：48

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 41期

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

页码：13603 / 13607

页数：5

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