Highly Site-Selective Direct C-H Bond Functionalization of Phenols with α-Aryl-α-diazoacetates and Diazooxindoles via Gold Catalysis

被引：380

作者：

Yu, Zhunzhun ^{[1
]}

Ma, Ben ^{[1
]}

Chen, Mingjin ^{[1
]}

Wu, Hai-Hong ^{[1
]}

Liu, Lu ^{[1
]}

Zhang, Junliang ^{[1
]}

机构：

[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Dept Chem, Shanghai 200062, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 19期

基金：

中国国家自然科学基金;

关键词：

INSERTION REACTIONS; CYCLOPROPANATION REACTIONS; DIAZO-COMPOUNDS; ENANTIOSELECTIVE INSERTION; ETHYL DIAZOACETATE; CARBENE INSERTION; ORGANIC-REACTIONS; DIRECT ARYLATION; METAL CARBENE; DERIVATIVES;

D O I：

10.1021/ja503163k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented direct C H bond functionalization of unprotected phenols with alpha-aryl alpha-diazoacetates and diazooxindoles was developed. A tris(2,4-di-tert-butylphenyl) phosphite derived gold complex promoted the highly chemoselective and site-selective C H bond functionalization of phenols and N-acylanilines with gold-carbene generated from the decomposition of diazo compounds, furnishing the corresponding products in moderate to excellent yields at rt. The salient features of this reaction include readily available starting materials, unprecedented C H functionalization rather than X H insertion, good substrate scope, mild conditions, high efficiency, and ease in further transformation. To the best of our knowledge, this is the first example of C H functionalization of unprotected phenols with diazo compounds.

引用

页码：6904 / 6907

页数：4

共 84 条

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