Iron(III)/Iodine-Catalyzed C(sp2)-H Activation of α,β-Unsaturated Aldehydes/Ketones with Amidines: Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles

被引：40

作者：

Wu, Ping ^{[1
,2
]}

Qu, Jinpeng ^{[1
,2
]}

Li, Yaxuan ^{[1
,2
]}

Guo, Xin ^{[1
,2
]}

Tang, Dong ^{[1
,2
]}

Meng, Xu ^{[3
]}

Yan, Rulong ^{[1
,2
]}

Chen, Baohua ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou, Gansu, Peoples R China

[2] Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou 730000, Peoples R China

[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 18期

基金：

中国国家自然科学基金;

关键词：

C-N bond formation; cross-dehydrogenative-coupling (CDC) reaction; highly substituted imidazoles; iron(III) catalysis; alpha; beta-unsaturated aldehydes/ketones; ONE-POT SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; CATALYZED DIRECT CYANATION; SP(3) C-H; MULTICOMPONENT SYNTHESIS; SUBSTITUTED IMIDAZOLES; HIGHLY EFFICIENT; MICHAEL REACTION; COPPER; ACID;

D O I：

10.1002/adsc.201500701

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient methodology to access a library of 1,2,4,5-tetrasubstituted imidazoles from a broad range of amidines and alpha,beta-unsaturated aldehydes/ketones via a C(sp(2)) H amination has been developed. This method represents a new and simple way to prepare highly substituted imidazoles from easily available starting materials, inexpensive catalysts, and with good functional group tolerance in good to excellent yields.

引用

页码：3868 / 3874

页数：7

共 85 条

[1]

[Anonymous], 2014, Angew. Chem

[2]

[Anonymous], 2008, ANGEW CHEM

[3]

[Anonymous], J CHEM SOC T

[4] 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

[5] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[6]

BURSTEIN C, 2004, ANGEW CHEM, V116, P6331

[7] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].

Campos, Kevin R. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084

[8] Iodine-catalyzed C-H/S-H oxidative coupling: from 1,3-diketones and thiophenols to β-dicarbonyl thioethers [J].

Cao, Hao ;

Yuan, Jiwen ;

Liu, Chao ;

Hu, Xinquan ;

Lei, Aiwen .

RSC ADVANCES, 2015, 5 (52) :41493-41496

[9] Synthesis of 2,4,5-triarylimidazoles in aqueous solution, under microwave irradiation [J].

Chauveau, Edouard ;

Marestin, Catherine ;

Schiets, Frederic ;

Mercier, Regis .

GREEN CHEMISTRY, 2010, 12 (06) :1018-1022

[10] Metal-Free, Acid-Promoted Synthesis of Imidazole Derivatives via a Multicomponent Reaction [J].

Chen, Chung-Yu ;

Hu, Wan-Ping ;

Yan, Pi-Cheng ;

Senadi, Gopal Chandru ;

Wang, Jeh-Jeng .

ORGANIC LETTERS, 2013, 15 (24) :6116-6119

← 1 2 3 4 5 6 7 8 9 →