CuI/BF3•Et2O Cocatalyzed Aerobic Dehydrogenative Reactions of Ketones with Benzylamines: Facile Synthesis of Substituted Imidazoles

被引：72

作者：

Cai, Zhong-Jian ^{[1
]}

Wang, Shun-Yi ^{[1
]}

Ji, Shun-Jun ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 23期

基金：

中国国家自然科学基金;

关键词：

COPPER-CATALYZED OXIDATION; ONE-POT SYNTHESIS; N BOND FORMATION; MOLECULAR-OXYGEN; C-N; REGIOSELECTIVE SYNTHESIS; ALPHA-KETOAMIDES; CYCLIZATION; FUNCTIONALIZATION; PALLADIUM;

D O I：

10.1021/ol302955u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel CuI/BF3 center dot Et2O/O-2-mediated reaction utilizing ketones and benzylamines for the construction of substituted imidazoles in one step under mild conditions has been demonstrated. This protocol involved the removal of eight hydrogen atoms, the functionalization of four C(sp(3))-H bonds and three new C-N bond formations.

引用

页码：6068 / 6071

页数：4

共 81 条

[1] [Anonymous], BER DTSCH CHEM GES
[2] [Anonymous], HETEROCYCLES
[3] [Anonymous], COMPREHENSIVE HETERO
[4] Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents.
Antolini, M
Bozzoli, A
Ghiron, C
Kennedy, G
Rossi, T
Ursini, A
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) : 1023 - 1028
[5] Aerobic and Electrochemical Oxidative Cross-Dehydrogenative-Coupling (CDC) Reaction in an Imidazolium-Based Ionic Liquid
Basle, Olivier
Borduas, Nadine
Dubois, Pauline
Chapuzet, Jean Marc
Chan, Tak-Hang
Lessard, Jean
Li, Chao-Jun
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 8162 - 8166
[6] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
Basle, Olivier
Li, Chao-Jun
[J]. CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
[7] Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles
Bellina, Fabio
Cauteruccio, Silvia
Rossi, Renzo
[J]. TETRAHEDRON, 2007, 63 (22) : 4571 - 4624
[8] Regioselective Functionalization of the Imidazole Ring via Transition Metal-Catalyzed C-N and C-C Bond Forming Reactions
Bellina, Fabio
Rossi, Renzo
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) : 1223 - 1276
[9] STUDIES ON WALLACHS IMIDAZOLE SYNTHESIS
BENINCORI, T
BRENNA, E
SANNICOLO, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (06): : 675 - 679
[10] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
Brasche, Gordon
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934

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