Recyclable copper catalyzed nitrogenation of biphenyl halides: a direct approach to carbazoles

被引：56

作者：

Ou, Yang ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 33期

基金：

美国国家科学基金会;

关键词：

N BOND FORMATION; C-H BONDS; ARYL AZIDES; DIRECT AMINATION; RH-2(II)-CATALYZED SYNTHESIS; SINGLE-ELECTRON; CARBON-CARBON; FUNCTIONALIZATION; BETA; ROUTE;

D O I：

10.1039/c3cc41443d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C-H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle.

引用

页码：3473 / 3475

页数：3

共 63 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2] Rapid synthesis of aryl azides from aryl halides under mild conditions [J].

Andersen, J ;

Madsen, U ;

Björkling, F ;

Liang, XF .

SYNLETT, 2005, (14) :2209-2213

[3] Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes [J].

Bhunia, Anup ;

Yetra, Santhivardhana Reddy ;

Biju, Akkattu T. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3140-3152

[4] Imidazole and benzimidazole derivatives as chemotherapeutic agents [J].

Boiani, M ;

González, M .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (04) :409-424

[5] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[6] ORGANOBORANES FOR SYNTHESIS .8. REACTION OF ORGANOBORANES WITH REPRESENTATIVE ORGANIC AZIDES - A GENERAL STEREOSPECIFIC SYNTHESIS OF SECONDARY-AMINES AND N-SUBSTITUTED AZIRIDINES [J].

BROWN, HC ;

MIDLAND, MM ;

LEVY, AB ;

SUZUKI, A ;

SONO, S ;

ITOH, M .

TETRAHEDRON, 1987, 43 (18) :4079-4088

[7] High-yielding intramolecular direct arylation reactions with aryl chlorides [J].

Campeau, LC ;

Thansandote, P ;

Fagnou, K .

ORGANIC LETTERS, 2005, 7 (09) :1857-1860

[8] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[9] Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].

Cho, Seung Hwan ;

Yoon, Jungho ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005

[10] Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Lee, S. Yunmi ;

Chang, Sukbok .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9127-9130

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