A Simple Copper-Catalyzed Synthesis of Tertiary Acyclic Amides

被引：72

作者：

Racine, Emilie ^{[1
]}

Monnier, Florian ^{[1
]}

Vors, Jean-Pierre ^{[2
]}

Taillefer, Marc ^{[1
]}

机构：

[1] Ecole Natl Super Chim Montpellier, CNRS, Inst Charles Gerhardt, UMR 5253,AM2N, F-34296 Montpellier 05, France

[2] Bayer CropSci SA, F-69005 Lyon, France

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 11期

关键词：

ARYL HALIDES; N-ARYLATION; COUPLING REACTIONS; IODIDES; AMIDATION; EFFICIENT; BROMIDES; PHENOLS; LIGANDS;

D O I：

10.1021/ol200750p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-arylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper catalytic system. The corresponding tertiary acyclic amides, which can be found in numerous biologically active compounds, have been obtained in good to excellent yields.

引用

页码：2818 / 2821

页数：4

共 24 条

[1] Copper-Catalyzed One-Pot Multicomponent Coupling Reaction of Phenols, Amides, and 4-Bromphenyl Iodide [J].

Chen, Wenming ;

Li, Jianjun ;

Fang, Dongimei ;

Feng, Chun ;

Zhang, Chenggang .

ORGANIC LETTERS, 2008, 10 (20) :4565-4568

[2] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

[3] Amino acid-mediated Goldberg reactions between amides and aryl iodides [J].

Deng, W ;

Wang, YF ;

Zou, W ;

Liu, L ;

Guo, QX .

TETRAHEDRON LETTERS, 2004, 45 (11) :2311-2315

[4] Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].

Evano, Gwilherm ;

Blanchard, Nicolas ;

Toumi, Mathieu .

CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131

[5] On phenylation of primary aromatic amines. [J].

Goldberg, I .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1907, 40 :4541-4546

[6] Concerning phenylization in the presence of copper as a catalytic agent. [J].

Goldberg, I .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1906, 39 :1691-1692

[7] Pd-Catalyzed N-Arylation of Secondary Acyclic Amides: Catalyst Development, Scope, and Computational Study [J].

Hicks, Jacqueline D. ;

Hyde, Alan M. ;

Cuezva, Alberto Martinez ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (46) :16720-16734

[8] Pd-catalyzed amidations of aryl chlorides using monodentate biaryl phosphine ligands: A kinetic, computational, and synthetic investigation [J].

Ikawa, Takashi ;

Barder, Timothy E. ;

Biscoe, Mark R. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) :13001-13007

[9] A general and efficient copper catalyst for the amidation of aryl halides [J].

Klapars, A ;

Huang, XH ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7421-7428

[10] Microwave-enhanced Goldberg reaction:: a novel route to N-arylpiperazinones and N-arylpiperazinediones [J].

Lange, JHM ;

Hofmeyer, LJF ;

Hout, FAS ;

Osnabrug, SJM ;

Verveer, PC ;

Kruse, CG ;

Feenstra, RW .

TETRAHEDRON LETTERS, 2002, 43 (06) :1101-1104

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