Copper-Catalyzed Oxidative Amination of sp3 C-H Bonds under Air: Synthesis of 1,3-Diarylated Imidazo[1,5-α]pyridines

被引：69

作者：

Wang, Huiqiao ^{[1
]}

Xu, Wentao ^{[1
]}

Wang, Zhiqiang ^{[1
]}

Yu, Lintao ^{[1
]}

Xu, Kun ^{[1
]}

机构：

[1] Nanyang Normal Univ, Coll Chem & Pharmaceut Engn, Nanyang 473061, Henan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 04期

关键词：

METAL-FREE; EFFICIENT SYNTHESIS; C(SP(3))-H; FUNCTIONALIZATION; CYCLIZATION; ALDEHYDES; ALCOHOLS; KETONES; BENZIMIDAZOLES; BENZOTHIAZOLES;

D O I：

10.1021/jo5027723

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper(II)-catalyzed tandem reaction between pyridine ketone and benzylamine was developed by using clean O-2 as an oxidant. This transformation proceeded via an efficient condensationaminationoxidative dehydrogenation process, affording 1,3-diarylated imidazo[1,5-a]pyridines in excellent yields.

引用

页码：2431 / 2435

页数：5

共 51 条

[1] Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles [J].

Armstrong, Alan ;

Collins, James C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) :2282-2285

[2] A NEW CLASS OF SYMPATHETIC BETA-RECEPTOR BLOCKING AGENTS - 3,4-DIHYDRO-3-HYDROXY-1,5-BENZOXAZOCINES [J].

BASIL, B ;

COFFEE, ECJ ;

GELL, DL ;

MAXWELL, DR ;

SHEFFIEL.DJ ;

WOOLDRID.KR .

JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (03) :403-&

[3] HETEROCYCLIC SYSTEMS RELATED TO PYRROCOLINE .1. 2-3A-DIAZAINDENE [J].

BOWER, JD ;

RAMAGE, GR .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :2834-2837

[4]

Bradman W., 1966, RECL TRAV CHIM PAY B, V85, P257

[5] Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts [J].

Che, Chi-Ming ;

Lo, Vanessa Kar-Yan ;

Zhou, Cong-Ying ;

Huang, Jie-Sheng .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1950-1975

[6] Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO [J].

Chen, Yong-Xing ;

Qian, Ling-Feng ;

Zhang, Wei ;

Han, Bing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) :9330-9333

[7] 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

[8] Catalytic C-H amination: the stereoselectivity issue [J].

Collet, Florence ;

Lescot, Camille ;

Dauban, Philippe .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1926-1936

[9] Catalytic C-H amination: recent progress and future directions [J].

Collet, Florence ;

Dodd, Robert H. ;

Dauban, Philippe .

CHEMICAL COMMUNICATIONS, 2009, (34) :5061-5074

[10] Recent advances in catalytic intramolecular C-H aminations [J].

Davies, HML ;

Long, MS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3518-3520

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