Metal-Free Oxidation/C(sp3)-H Functionalization of Unactivated Alkynes Using Pyridine-N-Oxide as the External Oxidant

被引：137

作者：

Chen, Dian-Feng ^{[1
,2
]}

Han, Zhi-Yong ^{[1
,2
]}

He, Yu-Ping ^{[1
,2
]}

Yu, Jie ^{[1
,2
]}

Gong, Liu-Zhu ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 49期

基金：

中国博士后科学基金;

关键词：

Bronsted acid; C-H functionalization; hydride transfer; metal-free reactions; oxidation; H BOND FUNCTIONALIZATION; CATALYZED CYCLOISOMERIZATION; ASYMMETRIC-SYNTHESIS; HYDROGEN SHIFT; GOLD; PLATINUM; CIS-3-EN-1-YNES; DERIVATIVES; ALKYLATION; ETHERS;

D O I：

10.1002/anie.201205062

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Externally yours: 2,3-Dihydroquinolin-4(1H)-ones are obtained in moderate to good yields (40-84 %, see scheme) in a metal-free oxidation/C(sp 3)iH functionalization of unactivated aryl alkynes. 2,6-Dichloropyridine-N-oxide is used as an external oxidant. In the reaction, a Brønsted acid, not a metal, plays a key role in the triple CiC bond activation. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12307 / 12310

页数：4

共 62 条

[11] Advances in the macrolides and quinolones [J].

Boswell, FJ ;

Wise, R .

INFECTIOUS DISEASE CLINICS OF NORTH AMERICA, 1998, 12 (03) :647-+

[12] Catalytic Enantioselective tert-Aminocyclization by Asymmetric Binary Acid Catalysis (ABC): Stereospecific 1,5-Hydrogen Transfer [J].

Chen, Liujuan ;

Zhang, Long ;

Lv, Jian ;

Cheng, Jin-Pei ;

Luo, Sanzhong .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) :8891-8895

[13]

Chen X., 2009, ANGEW CHEM, V121, P5196

[14] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[15] A Two-Step, Formal [4+2] Approach toward Piperidin-4-ones via Au Catalysis [J].

Cui, Li ;

Peng, Yu ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) :8394-+

[16] Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[b]azepin-4-ones from Tertiary N-(But-3-ynyl)anilines [J].

Cui, Li ;

Zhang, Guozhu ;

Peng, Yu ;

Zhang, Liming .

ORGANIC LETTERS, 2009, 11 (06) :1225-1228

[17] Ruthenium-catalyzed cycloisomerization of cis-3-en-1-ynes to cyclopentadiene and related derivatives through a 1,5-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates [J].

Datta, S ;

Odedra, A ;

Liu, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11606-11607

[18] C-H bond functionalization in complex organic synthesis [J].

Godula, K ;

Sames, D .

SCIENCE, 2006, 312 (5770) :67-72

[19] Redox-Neutral Indole Annulation Cascades [J].

Haibach, Michael C. ;

Deb, Indubhusan ;

De, Chandra Kanta ;

Seidel, Daniel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) :2100-2103

[20] An Efficient [2+2+1] Synthesis of 2,5-Disubstituted Oxazoles via Gold-Catalyzed Intermolecular Alkyne Oxidation [J].

He, Weimin ;

Li, Chaoqun ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) :8482-8485

← 1 2 3 4 5 6 7 →