Copper-Catalyzed C-N Bond Formation with N-Heterocycles and Aryl Halides

被引：25

作者：

Boswell, Mikki G. ^{[1
]}

Yeung, Fanny G. ^{[1
]}

Wolf, Christian ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

SYNLETT | 2012年 / 08期

基金：

美国国家科学基金会;

关键词：

copper; cross-coupling; N-heterocycles; aryl halides; microwave; CROSS-COUPLING REACTIONS; NITROGEN-CONTAINING HETEROCYCLES; LONG-LIVED CATALYSTS; ROOM-TEMPERATURE; AMINO-ACID; PALLADIUM PRECATALYSTS; EFFICIENT CATALYST; ARYLBORONIC ACID; HIGHLY EFFICIENT; AQUEOUS AMMONIA;

D O I：

10.1055/s-0031-1290827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The microwave-assisted, cuprous oxide catalyzed coupling of aryl bromides and iodides with imidazole, benzimidazole, pyrazole, or triazole was found to give a wide range of N-aryl heteroaromatic products in good to high yields. Aryl dibromides undergo selective monosubstitution even in the presence of large excess of N-heterocyclic nucleophiles which leaves the second aryl bromide functionality intact for further derivatization.

引用

页码：1240 / 1244

页数：5

共 79 条

[51] Novel CuO nanoparticle catalyzed C-N cross coupling of amines with iodobenzene [J].

Rout, Laxmidhar ;

Jammi, Suribabu ;

Punniyamurthy, T. .

ORGANIC LETTERS, 2007, 9 (17) :3397-3399

[52] Air-Stable Pd(R-allyl)LCl (L = Q-Phos, P(t-Bu)3, etc.) Systems for C-C/N Couplings: Insight into the Structure Activity Relationship and Catalyst Activation Pathway [J].

Seechurn, Carin C. C. Johansson ;

Parisel, Sebastien L. ;

Colacot, Thomas J. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :7918-7932

[53] Highly selective room-temperature copper-catalyzed C-N coupling reactions [J].

Shafir, Alexandr ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) :8742-8743

[54] [(CyPF-tBu)PdCl2]:: An air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides [J].

Shen, Qilong ;

Hartwig, John F. .

ORGANIC LETTERS, 2008, 10 (18) :4109-4112

[55] Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: Scope and structure-activity relationships [J].

Shen, Qilong ;

Ogata, Tokutaro ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (20) :6586-6596

[56] Lewis acid acceleration of C-N bond-forming reductive elimination from heteroarylpalladium complexes and catalytic amidation of heteroaryl bromides [J].

Shen, Qilong ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7734-+

[57] Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles [J].

Shen, QL ;

Shekhar, S ;

Stambuli, JP ;

Hartwig, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1371-1375

[58] Aromatic borylation/amidation/oxidation: A rapid route to 5-substituted 3-amidophenols [J].

Shi, F ;

Smith, MR ;

Maleczka, RE .

ORGANIC LETTERS, 2006, 8 (07) :1411-1414

[59] Copper(I) oxide catalyzed n-arylation of Azoles and Amines with arylboronic acid at room temperature under base-free conditions [J].

Sreedhar, Bojja ;

Venkanna, Gopaladasu T. ;

Kumar, Kota Balaji Shiva ;

Balasubrahmanyarn, Vura .

SYNTHESIS-STUTTGART, 2008, 5 (05) :795-799

[60] The role of chelating diamine ligands in the Goldberg reaction: A kinetic study on the copper-catalyzed amidation of aryl iodides [J].

Strieter, ER ;

Blackmond, DG ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4120-4121

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