Palladium-Catalyzed Highly Selective ortho-Halogenation (I, Br, Cl) of Arylnitriles via sp2 C-H Bond Activation Using Cyano as Directing Group

被引：124

作者：

Du, Bingnan ^{[1
]}

Jiang, Xiaoqing ^{[1
]}

Sun, Peipei ^{[1
,2
]}

机构：

[1] Nanjing Normal Univ, Coll Chem & Mat Sci, Jiangsu Key Lab Biofunct Mat, Nanjing 210097, Jiangsu, Peoples R China

[2] Nanjing Normal Univ, Key Lab Appl Photochem, Nanjing 210097, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; ARYLATION; ARYL; IODINATION; COMPLEXES; HALIDES; KETONES;

D O I：

10.1021/jo302765g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed ortho-halogenation (I, Br, Cl) of arylnitrile is described. The optimal reaction conditions were identified after examining various factors such as catalyst, additive, solvent, and reaction temperature. Using cyano as the directing group, the halogenation reaction gave good to excellent yields. The method is compatible to the arylnitriles with either electron-withdrawing or electron-donating groups. The reaction is available to the substrate in at least gram scale. The present method was successfully applied to the synthesis of the precursors of paucifloral F and isopaucifloral F.

引用

页码：2786 / 2791

页数：6

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