Gold-Catalyzed syn-1,2-Difunctionalization of Ynamides via Nitrile Activation

被引：64

作者：

Vanjari, Rajeshwer ^{[1
]}

Dutta, Shubham ^{[1
]}

Gogoi, Manash P. ^{[1
]}

Gandon, Vincent ^{[2
,3
]}

Sahoo, Akhila K. ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

[2] Univ Paris Saclay, Univ Paris Sud, ICMMO, CNRS,UMR 8182, Batiment 420, F-91405 Orsay, France

[3] Univ Paris Saclay, Ecole Polytech, LCM, CNRS,UMR 9168, Route Saclay, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 24期

关键词：

DUAL-ACTIVATION; RAPID ACCESS; CYCLIZATION; CYCLOISOMERIZATION; ALKYNES;

D O I：

10.1021/acs.orglett.8b03830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Developed is an unprecedented Au(I)-catalyzed syn-1,2-difunctionalization of ynamides with 2-amino-benzonitriles via nitrile activation. The coupling between ynamides and 2-aminobenzonitriles is explicitly regioselective, providing a straightforward access to 2,4-diamino-substituted quinolines. Density functional theory (DFT) study provides insightful information and rationalizes the reaction pathway. It shows how the synergy between ynamide pi-activation and nitrile sigma-coordination by the Au(I) catalyst makes the cyclization viable.

引用

页码：8077 / 8081

页数：5

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