Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles

被引：15

作者：

Gong, Julin ^{[1
]}

Hu, Kun ^{[1
]}

Shao, Yinlin ^{[1
]}

Li, Renhao ^{[2
]}

Zhang, Yetong ^{[1
]}

Hu, Maolin ^{[1
]}

Chen, Jiuxi ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Wenzhou Med Univ, Sch Pharmaceut Sci, Wenzhou 325035, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 03期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM-CATALYZED ADDITION; ARYL KETONES; ARYLBORONIC ACIDS; C-H; PALLADIUM(II)-CATALYZED SYNTHESIS; ALDEHYDES; COMPLEXES; SOLVENTS; GREEN; INHIBITORS;

D O I：

10.1039/c9ob02408e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2-(2-acylphenoxy)-1-phenylethan-1-one followed by an intramolecular cyclization. This methodology has also been applied to the synthesis of 2-aroyl indoles and the potent CYP19 inhibitor 1-(benzofuran-2-yl(phenyl)methyl)-1H-1,2,4-triazole.

引用

页码：488 / 494

页数：7

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