A Cross-Coupling Approach to Amide Bond Formation from Esters

被引：131

作者：

Ben Halima, Taoufik ^{[1
]}

Vandavasi, Jaya Kishore ^{[1
]}

Shkoor, Mohanad ^{[1
,2
]}

Newman, Stephen G. ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem & Biomol Sci, Ctr Catalysis Res & Innovat, 10 Marie Curie, Ottawa, ON K1N 6N5, Canada

[2] Qatar Univ, Coll Arts & Sci, Dept Chem & Earth Sci, POB 2713, Doha, Qatar

来源：

ACS CATALYSIS | 2017年 / 7卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

cross-coupling amides; palladium catalysis; C-O bond activation; C-N coupling; CATALYZED DECARBONYLATIVE BORYLATION; C-O ACTIVATION; ARYL ESTERS; NICKEL CATALYSIS; ATMOSPHERIC-PRESSURE; PHENOL DERIVATIVES; ORGANOBORON COMPOUNDS; ARYLBORONIC ACIDS; KETONE SYNTHESIS; BORONIC ACIDS;

D O I：

10.1021/acscatal.7b00245

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C-O bond by oxidative addition with a Pd-NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic, and heterocyclic products are obtained. A range of activated esters are evaluated in the presence and absence of catalyst, demonstrating that the catalytic methodology substantially increases the types of electrophiles that can be utilized for amide bond formation the absence of harsh bases.

引用

页码：2176 / 2180

页数：5

共 77 条

[1] Metal-catalysed approaches to amide bond formation [J].