Nickel-catalyzed Amide Transformation via C-N Bond Cleavage

被引：0

作者：

Nishii, Yuji

机构：

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2016年 / 74卷 / 08期

关键词：

CROSS-COUPLING REACTION; KETONE SYNTHESIS; ORGANOBORON COMPOUNDS; CARBOXYLIC-ACIDS; ESTERS; ANHYDRIDES; ACTIVATION; COMPLEXES;

D O I：

10.5059/yukigoseikyokaishi.74.824

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acyl metal species generated from carboxylic acid derivatives upon treating with low valent transition-metal complexes have been utilized for various catalytic transformations. Recently, it was revealed that a catalyst system of Ni(0)/NHC (N-Heterocyclic Carbene) triggered amide C-N bond cleavage via oxidative addition to afford acyl nickel complexes. The obtained acyl species were further converted into the corresponding esters and ketones in catalytic manner. A proposed reaction mechanism and some synthetic applications are concisely summarized herein.

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页码：824 / 825

页数：2

相关论文

共 14 条

[1] Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].

Amaike, Kazuma ;

Muto, Kei ;

Yamaguchi, Junichiro ;

Itami, Kenichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576

[2]

Goossen LJ, 2001, CHEM COMMUN, P2084

[3]

Goossen LJ, 2001, ANGEW CHEM INT EDIT, V40, P3458, DOI 10.1002/1521-3773(20010917)40:18<3458::AID-ANIE3458>3.0.CO

[4]

2-0

[5] A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids [J].

Haddach, M ;

McCarthy, JR .

TETRAHEDRON LETTERS, 1999, 40 (16) :3109-3112

[6] Conversion of amides to esters by the nickel-catalysed activation of amide C-N bonds [J].

Hie, Liana ;

Nathel, Noah F. Fine ;

Shah, Tejas K. ;

Baker, Emma L. ;

Hong, Xin ;

Yang, Yun-Fang ;

Liu, Peng ;

Houk, K. N. ;

Garg, Neil K. .

NATURE, 2015, 524 (7563) :79-83

[7] Synthesis of unsymmetrical ketones by palladium-catalyzed cross-coupling reaction of carboxylic anhydrides with organoboron compounds [J].

Kakino, R ;

Yasumi, S ;

Shimizu, I ;

Yamamoto, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (01) :137-148

[8] 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

[9] Thiol ester-boronic acid coupling. A mechanistically unprecedented and general ketone synthesis [J].

Liebeskind, LS ;

Srogl, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (45) :11260-11261

[10] Sterically Controlled Pd-Catalyzed Chemoselective Ketone Synthesis via N-C Cleavage in Twisted Amides [J].

Meng, Guangrong ;

Szostak, Michal .

ORGANIC LETTERS, 2015, 17 (17) :4364-4367