Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary

被引：124

作者：

Li, Xin ^{[1
]}

Liu, Yan-Hua ^{[1
]}

Gu, Wen-Jia ^{[1
]}

Li, Bo ^{[1
]}

Chen, Fa-Jie ^{[1
]}

Shi, Bing-Feng ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 15期

基金：

美国国家科学基金会;

关键词：

C-H BONDS; UNACTIVATED C(SP(3))-H; OXIDATIVE OLEFINATION; CATALYZED ARYLATION; PALLADIUM; FUNCTIONALIZATION; AMINATION; AMIDATION; ALKYNYLATION; OXYGENATION;

D O I：

10.1021/ol5016064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-mediated C-H hydroxylation of arenes and heteroarenes using our newly developed PIP directing group has been developed. This procedure is scalable and compatible with a wide range of functional groups and heteroarenes, providing an operationally simple protocol for the synthesis of o-hydroxybenzamides. The hydroxylation of nicotinamides gave 4-oxo-1,4-dihydropyridine-3-carboxamides selectively. Preliminary mechanistic studies implicate that a basic ligand-enabled, irreversible, rate-determining CMD step is most likely involved in this process.

引用

页码：3904 / 3907

页数：4

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