Palladium-Catalyzed Selective Dehydrogenative Cross-Couplings of Heteroarenes

被引：152

作者：

Bugaut, Xavier ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 33期

关键词：

biaryls; C-H bond activation; heterocycles; oxidative cross-coupling; palladium; DIRECT ARYLATION; PRECATALYST; MECHANISM; AZINE;

D O I：

10.1002/anie.201103106

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nice couple: Two heteroaryls bearing no prefunctionalization can be cross-coupled efficiently through Pd II catalysis to afford the biheteroaryl. The selectivity of this transformation probably finds its origin in the two mechanistically different metalation steps of Ci-H bonds. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7479 / 7481

页数：3

共 23 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[4]

[Anonymous], ANGEW CHEM

[5]

[Anonymous], ANGEW CHEM

[6] Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation [J].

García-Cuadrado, D ;

Braga, AAC ;

Maseras, F ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1066-1067

[7] Palladium-Catalyzed Oxidative Cross-Coupling between Pyridine N-Oxides and Indoles [J].

Gong, Xue ;

Song, Guoyong ;

Zhang, Hong ;

Li, Xingwei .

ORGANIC LETTERS, 2011, 13 (07) :1766-1769

[8] Palladium-Catalyzed Dehydrogenative Cross-Couplings of Benzazoles with Azoles [J].

Han, Wei ;

Mayer, Peter ;

Ofial, Armin R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) :2178-2182

[9] A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids [J].

Kinzel, Tom ;

Zhang, Yong ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14073-14075

[10] Metal-Free Oxidative Cross-Coupling of Unfunctionalized Aromatic Compounds [J].

Kita, Yasuyuki ;

Morimoto, Koji ;

Ito, Motoki ;

Ogawa, Chieko ;

Goto, Akihiro ;

Dohi, Toshifumi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) :1668-+

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