Steric, Electronic and Conformational Synergistic Effects in the Gold(I)-catalyzed α-C-H Bond Functionalization of Tertiary Amines

被引：39

作者：

Rayo, David F. Leon ^{[1
]}

Mansour, Ali ^{[1
]}

Wu, Wenbin ^{[2
]}

Bhawal, Benjamin N. ^{[2
,3
]}

Gagosz, Fabien ^{[1
,2
]}

机构：

[1] Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada

[2] Ecole Polytech, Dept Chim, UMR 7652 CNRS, F-91128 Palaiseau, France

[3] Univ Edinburgh, Sch Chem, EaStChem, Joseph Black Bldg,David Brewster Rd, Edinburgh EH9 3FJ, Midlothian, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Amines; C-H Bond Functionalization; Gold Catalysis; Hydride Shift; Tetrahydro-gamma-Carbolines; UNACTIVATED C(SP(3))-H BONDS; GOLD-CATALYZED SYNTHESIS; HYDRIDE SHIFT; CARBENES; INSERTION; ACCESS; PSEUDOINDOXYL; CYCLIZATION; ACTIVATION; GENERATION;

D O I：

10.1002/anie.202212893

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct C-H bond functionalization is a useful strategy for the straightforward formation of C-C and C-Heteroatom bonds. In the present work, a unique approach for the challenging electrophilic Au-catalyzed alpha-C-H bond functionalization of tertiary amines is presented. Electronic, steric and conformational synergistic effects exerted by the use of a malonate unit in the substrate were key to the success of this transformation. This new reactivity was applied to the synthesis of tetrahydro-gamma-carboline products which, under oxidative conditions, could be converted into valuable structural motifs found in bioactive alkaloid natural products.

引用

页数：10

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