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

被引：46

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

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