Rhodium(III)-Catalyzed Oxidative Olefination of Pyridines and Quinolines: Multigram-Scale Synthesis of Naphthyridinones

被引：95

作者：

Zhou, Jun ^{[1
]}

Li, Bo ^{[1
]}

Hu, Fang ^{[2
]}

Shi, Bing-Feng ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 13期

基金：

美国国家科学基金会;

关键词：

C-H FUNCTIONALIZATION; DIRECT ARYLATION; SELECTIVE ALKENYLATION; CATALYZED REACTION; BOND FORMATION; N-OXIDES; ALKYNES; ALKYLATION; ACTIVATION; REAGENTS;

D O I：

10.1021/ol401540k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(III)-catalyzed oxidative olefination of pyridines and quinolines has been achieved. This method has a broad substrate scope and has been applied to the expeditious, multigram-scale synthesis of naphthyridinones.

引用

页码：3460 / 3463

页数：4

共 61 条

[1]

Alemparte-Gallardo C, 2009, International patent application, Patent No. [WO 2009/141399 A1, 20091126, 2009141399]

[2]

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

[3] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].

Berman, Ashley M. ;

Lewis, Jared C. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+

[4] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[5] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[6] Rh(III)-Catalyzed Oxidative Coupling of N-Aryl-2-aminopyridine with Alkynes and Alkenes [J].

Chen, Jinlei ;

Song, Guoyong ;

Pan, Cheng-Ling ;

Li, Xingwei .

ORGANIC LETTERS, 2010, 12 (23) :5426-5429

[7] 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-+

[8] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[9] Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions [J].

Engle, Keary M. ;

Mei, Tian-Sheng ;

Wasa, Masayuki ;

Yu, Jin-Quan .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :788-802

[10]

Ferreira E.M., 2009, MIZOROKI HECK REACTI, P345

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