Transition-Metal-Free Tunable Chemoselective N Functionalization of Indoles with Ynamides

被引：50

作者：

Hentz, Alexandre ^{[1
]}

Retailleau, Pascal ^{[1
]}

Gandon, Vincent ^{[1
,2
]}

Cariou, Kevin ^{[1
]}

Dodd, Robert H. ^{[1
]}

机构：

[1] CNRS, UPR 2301, LabEx LERMIT, Ctr Rech Gif Sur Yvette,Inst Chim Subst Nat,UPR 2, F-91198 Gif Sur Yvette, France

[2] Univ Paris 11, CNRS, UMR 8182, ICMMO,LabEx CHARMMMAT, F-91405 Orsay, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 32期

关键词：

alkynes; density functional calculations; heterocycles; reaction mechanisms; synthetic methods; STEREOSELECTIVE CIS-HYDROARYLATION; DIPHENYLDITHIOPHOSPHINIC ACID; ALCOHOLS; VINYLINDOLES; ADDITIONS; ENAMINES;

D O I：

10.1002/anie.201402767

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two unprecedented N functionalizations of indoles with ynamides are described. By varying the electron-with-drawing group on the ynamide nitrogen atom, either Z-indolo-etheneamides or indolo-amidines can be selectively obtained under the same metal-free reaction conditions. The scope and synthetic potential of these reactions, as well as some mechanistic insights provided by DFT calculations, are reported.

引用

收藏

页码：8333 / 8337

页数：5

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