General Method for the Suzuki Miyaura Cross-Coupling of Amides Using Commercially Available, Air-and Moisture-Stable Palladium/ NHC (NHC = N-Heterocyclic Carbene) Complexes

被引：164

作者：

Lei, Peng ^{[1
,2
]}

Meng, Guangrong ^{[1
]}

Szostak, Michal ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA

[2] China Agr Univ, Coll Sci, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

ACS CATALYSIS | 2017年 / 7卷 / 03期

关键词：

palladium; N-heterocyclic carbenes (NHCs); N-C activation; Suzuki Miyaura cross-coupling; amides; ARYL CHLORIDES; TWISTED AMIDES; BOND-CLEAVAGE; CATALYZED ACTIVATION; BUCHWALD-HARTWIG; KETONE SYNTHESIS; C CLEAVAGE; NITROGEN; REAGENTS; LIGANDS;

D O I：

10.1021/acscatal.6b03616

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：

The direct Suzuki Miyaura cross-coupling of amides catalyzed by Pd-NHC complexes is reported. Using a single protocol, commercially available, air-and moisture stable (NHC)Pd(R-allyl)Cl complexes can effect Suzuki Miyaura cross-coupling of a wide range of amides with arylboronic acids in very good yields. The studies described herein represent the use of versatile Pd-NHC complexes as catalysts for transition-metal-catalyzed cross-coupling of amides by N-C bond activation. The Pd-NHC catalysts provide a significant improvement over all current Pd-PR3 systems employed for the amide N -C bond activation. Mechanistic studies provide strong support for the development of a unified reactivity scale of the amide bond for the generation of aryl-metal intermediates.

引用

页码：1960 / 1965

页数：6

共 80 条

[31] Structural Characterization of N-Alkylated Twisted Amides: Consequences for Amide Bond Resonance and N-C Cleavage [J].

Hu, Feng ;

Lalancette, Roger ;

Szostak, Michal .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (16) :5062-5066

[32] Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C-N Bond Activation [J].

Hu, Jiefeng ;

Zhao, Yue ;

Liu, Jingjing ;

Zhang, Yemin ;

Shi, Zhuangzhi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) :8718-8722

[33] Efficient cross-coupling of aryl chlorides with aryl grignard reagents (Kumada reaction) mediated by a palladium/imidazolium chloride system [J].

Huang, JK ;

Nolan, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (42) :9889-9890

[34] Understanding the M-(NHC) (NHC = N-heterocyclic carbene) bond [J].

Jacobsen, Heiko ;

Correa, Andrea ;

Poater, Albert ;

Costabile, Chiara ;

Cavallo, Luigi .

COORDINATION CHEMISTRY REVIEWS, 2009, 253 (5-6) :687-703

[35] Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions - A synthetic chemist's perspective [J].

Kantchev, Eric Assen B. ;

O'Brien, Christopher J. ;

Organ, Michael G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (16) :2768-2813

[36] Selection of boron reagents for Suzuki-Miyaura coupling [J].

Lennox, Alastair J. J. ;

Lloyd-Jones, Guy C. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (01) :412-443

[37] Development of Preformed Pd Catalysts for Cross-Coupling Reactions, Beyond the 2010 Nobel Prize [J].

Li, Hongbo ;

Seechurn, Carin C. C. Johansson ;

Colacot, Thomas J. .

ACS CATALYSIS, 2012, 2 (06) :1147-1164

[38] Acylative Suzuki coupling of amides: acyl-nitrogen activation via synergy of independently modifiable activating groups [J].

Li, Xijing ;

Zou, Gang .

CHEMICAL COMMUNICATIONS, 2015, 51 (24) :5089-5092

[39] Twisted Amides: From Obscurity to Broadly Useful Transition-Metal-Catalyzed Reactions by N-C Amide Bond Activation [J].

Liu, Chengwei ;

Szostak, Michal .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (30) :7157-7173

[40] N-Acylsaccharins as Amide-Based Arylating Reagents via Chemoselective N-C Cleavage: Pd-Catalyzed Decarbonylative Heck Reaction [J].

Liu, Chengwei ;

Meng, Guangrong ;

Szostak, Michal .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) :12023-12030

← 1 2 3 4 5 6 7 8 →