Palladium-Catalyzed Direct Ortho Aroylation of 2-Phenoxypyridines with Aldehydes and Catalytic Mechanism Investigation

被引：47

作者：

Chu, Jean-Ho ^{[1
]}

Chen, Shih-Tien ^{[1
]}

Chiang, Meng-Fan ^{[1
]}

Wu, Ming-Jung ^{[1
]}

机构：

[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

ORGANOMETALLICS | 2015年 / 34卷 / 05期

关键词：

ALPHA-OXOCARBOXYLIC ACIDS; DECARBOXYLATIVE ORTHO-ACYLATION; C-H ACTIVATION; OXIDATIVE ORTHO-ACYLATION; TERT-BUTYL HYDROPEROXIDE; DIRECT ORTHO ARYLATION; O-METHYL OXIMES; DIRECT FUNCTIONALIZATION; BOND FUNCTIONALIZATIONS; TOLUENE DERIVATIVES;

D O I：

10.1021/om501330h

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A direct ortho aroylation of 2-phenoxypyridines with aldehydes leading to aryl ketones by the use of palladium(II) acetate, tert-butyl hydroperoxide, and chlorobenzene as the catalyst, oxidant, and solvent, respectively, is presented. Intra- and intermolecular kinetic isotope effects, radical trapping, and controlled experiments were carried out to support the proposed catalytic mechanism for the reaction. Syntheses of (2-hydroxyphenyl)(phenyl)methanones and 1-hydroxy-9H-fluoren-9-ones directed from ortho-aroylated 2-phenoxypyridines were demonstrated.

引用

页码：953 / 966

页数：14

共 67 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] Palladium-Catalyzed ortho-Aroylation of 2-Arylbenzothiazoles and 2-Arylbenzoxazoles with Aldehydes [J].

Banerjee, Arghya ;

Santra, Sourav Kumar ;

Guin, Srimanta ;

Rout, Saroj Kumar ;

Patel, Bhisma K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (07) :1367-1376

[4] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes [J].

Basle, Olivier ;

Bidange, Johan ;

Shuai, Qi ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) :1145-1149

[5] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[6] Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Yu, Wing-Yiu .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) :2999-3006

[7] Pd-Catalyzed Ortho-C HAcylation/Cross Coupling of Aryl Ketone O-Methyl Oximes with Aldehydes Using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Chan, Albert S. C. ;

Yu, Wing-Yiu .

ORGANIC LETTERS, 2010, 12 (17) :3926-3929

[8] 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

[9] Palladium-Catalyzed Arylation and Alkylation of 3,5-Diphenylisoxazole with Boronic Acids via C-H Activation [J].

Chu, Jean-Ho ;

Chen, Chin-Chau ;

Wu, Ming-Jung .

ORGANOMETALLICS, 2008, 27 (20) :5173-5176

[10] Substituent Electronic Effects Govern Direct Intramolecular C-N Cyclization of N-(Biphenyl)pyridin-2-amines Induced by Hypervalent lodine(III) Reagents [J].

Chu, Jean-Ho ;

Hsu, Wen-Ting ;

Wu, Yi-Hua ;

Chiang, Meng-Fan ;

Hsu, Nan-Hai ;

Huang, Hao-Ping ;

Wu, Ming-Jung .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23) :11395-11408

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