Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine N-Oxides from Oximes and Diazo Compounds

被引:402
作者
Shi, Zhuangzhi [1 ]
Koester, Dennis C. [1 ]
Boultadakis-Arapinis, Melissa [1 ]
Glorius, Frank [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
基金
欧洲研究理事会;
关键词
C-H BONDS; ONE-POT SYNTHESIS; ALPHA; BETA-UNSATURATED KETOXIMES; RHODIUM(III)-CATALYZED SYNTHESIS; REGIOSELECTIVE SYNTHESIS; INTERNAL ALKYNES; DIRECT ARYLATION; FUNCTIONALIZATION; ACTIVATION; ARYL;
D O I
10.1021/ja406338r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Multisubstituted isoquinoline and pyridine N-oxides have been prepared by Rh(III)-catalyzed cyclization of oximes and diazo compounds via aryl and vinylic C-H activation. This intermolecular annulation involving tandem C-H activation, cyclization, and condensation steps proceeds under mild conditions, obviates the need for oxidants, releases N-2 and H2O as the byproducts, and displays a broad substituent scope.
引用
收藏
页码:12204 / 12207
页数:4
相关论文
共 100 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]  
Albini A., 1991, HETEROCYCLIC N OXIDE
[3]  
[Anonymous], J NAT PROD
[4]  
[Anonymous], 2000, THE MERCK INDEX ON C
[5]   Rhodium-Catalyzed C-H Bond Arylation of Arenes [J].
Bouffard, Jean ;
Itami, Kenichiro .
C-H ACTIVATION, 2010, 292 :231-280
[6]   Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines [J].
Bull, James A. ;
Mousseau, James J. ;
Pelletier, Guillaume ;
Charette, Andre B. .
CHEMICAL REVIEWS, 2012, 112 (05) :2642-2713
[7]   Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].
Campeau, Louis-Charles ;
Schipper, Derek J. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+
[8]   Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].
Campeau, Louis-Charles ;
Stuart, David R. ;
Leclerc, Jean-Philippe ;
Bertrand-Laperle, Megan ;
Villemure, Elisia ;
Sun, Ho-Yan ;
Lasserre, Sandrine ;
Guimond, Nicolas ;
Lecavallier, Melanie ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306
[9]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[10]   Helical Chiral Pyridine N-Oxides: A New Family of Asymmetric Catalysts [J].
Chen, Jinshui ;
Takenaka, Norito .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (30) :7268-7276