Rhodium(III)-Catalyzed C-C Bond Formation of Quinoline N-Oxides at the C-8 Position under Mild Conditions

被引：202

作者：

Jeong, Jisu ^{[1
,2
]}

Patel, Pitambar ^{[1
,2
]}

Hwang, Heejun ^{[1
,2
]}

Chang, Sukbok ^{[1
,2
]}

机构：

[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea

[2] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Taejon 305701, South Korea

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 17期

关键词：

DIRECT ALKYNYLATION; H ALKYNYLATION; CARBENOID FUNCTIONALIZATION; RH(III)-CATALYZED SYNTHESIS; REGIOSELECTIVE SYNTHESIS; DIRECT ARYLATION; DIAZO-COMPOUNDS; PALLADIUM; ACTIVATION; ARYL;

D O I：

10.1021/ol502173d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh(III)-catalyzed C-8 selective direct alkylation and alkynylation of quinoline N-oxides has been developed. The reactions proceeded highly efficiently at room temperature over a broad range of substrates with excellent regioselectivity and functional group tolerance. This development demonstrates the synthetic utility of the N-oxide directing group as a stepping stone for remote C H functionalization of quinolines.

引用

页码：4598 / 4601

页数：4

共 84 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]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]

[3]

Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a

[4] Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Bronsted Acids [J].

Brand, Jonathan P. ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7304-7307

[5] Direct Alkynylation of Indole and Pyrrole Heterocycles [J].

Brand, Jonathan P. ;

Charpentier, Julie ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349

[6] 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

[7] 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

[8] Direct 2-acetoxylation of quinoline N-oxides via copper catalyzed C-H bond activation [J].

Chen, Xuan ;

Zhu, Chongwei ;

Cui, Xiuling ;

Wu, Yangjie .

CHEMICAL COMMUNICATIONS, 2013, 49 (61) :6900-6902

[9] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].

Cho, Seung Hwan ;

Hwang, Seung Jun ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+

[10] 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

← 1 2 3 4 5 6 7 8 9 →