Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMelHeptCl)Pd Promoted by Trialkylboranes or B(C6F5)3

被引：33

作者：

Sharif, Sepideh ^{[1
]}

Day, Jonathan ^{[1
]}

Hunter, Howard N. ^{[1
]}

Lu, Yu ^{[2
]}

Mitchell, David ^{[2
]}

Rodriguez, Michael J. ^{[2
]}

Organ, Michael G. ^{[1
,3
,4
]}

机构：

[1] York Univ, Dept Chem, 4700 Keele St, Toronto, ON M3J 1P3, Canada

[2] Lily Res Labs, Indianapolis, IN 46285 USA

[3] Univ Ottawa, CCRI, Ottawa, ON K1N 6N5, Canada

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 51期

基金：

加拿大自然科学与工程研究理事会;

关键词：

REDUCTIVE ELIMINATION; ROOM-TEMPERATURE; AMINATION; CATALYST; COMPLEXES; MECHANISM; PD-PEPPSI-IHEPT(CL); PD-PEPPSI-IPENT(CL); HYDROSTANNYLATION; ACCELERATION;

D O I：

10.1021/jacs.7b09488

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Boron-derived Lewis acids have been shown to effectively promote the coupling of amide nucleophiles to a wide variety of oxidative addition partners using Pd-NHC catalysts. Through a combination of NMR spectroscopy and control studies with and without oxygen and radical scavengers, we propose that boron-imidates form under the basic reaction conditions that aid coordination of nitrogen to Pd(II), which is rate limiting, and directly delivers the intermediate for reductive elimination.

引用

页码：18436 / 18439

页数：4

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