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

被引：120
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
收藏
页码：3904 / 3907
页数：4
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