One-Pot Synthesis of Heteroaryl and Diheteroaryl Ketones through Palladium-Catalyzed 1,2-Addition and Oxidation

被引：28

作者：

Kuriyama, Masami ^{[1
]}

Hamaguchi, Norihisa ^{[1
]}

Sakata, Keisuke ^{[1
]}

Onomura, Osamu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 16期

基金：

日本学术振兴会;

关键词：

Synthetic methods; Homogeneous catalysis; Nucleophilic addition; Palladium; Ketones; Heterocycles; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; ADDITION-REACTIONS; ORTHOPLATINATED TRIARYLPHOSPHITE; ALPHA; BETA-UNSATURATED KETONES; ALKENYLBORONIC ACIDS; DIARYL KETONES; ALDEHYDES; ARYL; EFFICIENT;

D O I：

10.1002/ejoc.201300269

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic method was developed for the preparation of heteroaryl and diheteroaryl ketones from aldehydes and organoboronic acids through a palladium-catalyzed 1,2-addition and oxidation that uses an aryl iodide as the oxidant. This one-pot process shows high tolerance for a broad range of heterocyclic substrates by using 1.0-3.0 mol-% of the catalyst that is formed from allylpalladium chloride dimer and a thioether-imidazolinium chloride. In addition to fine-tuning the catalytic system, the use of a sterically hindered aryl iodide that has a substituent at the ortho position, such as 2-iodotoluene, is important to obtain the desired ketones with heterocyclic moieties in good to excellent yields.

引用

页码：3378 / 3385

页数：8

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