Kinetic Modeling of the Nickel-Catalyzed Esterification of Amides

被引：66

作者：

Weires, Nicholas A. ^{[1
]}

Caspi, Daniel D. ^{[2
]}

Garg, Neil K. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] AbbVie Inc, Ctr React Engn, Res & Dev, 1 N Waukegan Rd, N Chicago, IL 60064 USA

来源：

ACS CATALYSIS | 2017年 / 7卷 / 07期

基金：

美国国家科学基金会;

关键词：

nickel; catalysis; cross-coupling; amides; kinetic modeling; N-C CLEAVAGE; NITROGEN BOND-CLEAVAGE; COUPLING REACTIONS; KETONE SYNTHESIS; ACTIVATION; FUNCTIONALIZATION; ACYLSACCHARINS; DERIVATIVES; DESIGN;

D O I：

10.1021/acscatal.7b01444

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：

Nickel-catalyzed coupling reactions provide exciting tools in chemical synthesis. However, most methodologies in this area require high catalyst loadings, which commonly range from 10-20 mol % nickel. Through an academic-industrial collaboration, we demonstrate that kinetic modeling can be used strategically to overcome this problem, specifically within the context of the Ni-catalyzed conversion of amides to esters. The successful application of this methodology to a multigram-scale coupling, using only 0.4 mol % Ni, highlights the impact of this endeavor.

引用

页码：4381 / 4385

页数：5

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