Protodeboronation of ortho- and para-Phenol Boronic Acids and Application to ortho and meta Functionalization of Phenols Using Boronic Acids as Blocking and Directing Groups

被引：55

作者：

Lee, Chun-Young ^{[1
]}

Ahn, Su-Jin ^{[1
]}

Cheon, Cheol-Hong ^{[1
]}

机构：

[1] Korea Univ, Dept Chem, Seoul 136701, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 23期

基金：

新加坡国家研究基金会;

关键词：

CROSS-COUPLING REACTIONS; C-H BORYLATION; ARYLBORONIC ACIDS; STEREOSELECTIVE-SYNTHESIS; ARENES; LIGAND;

D O I：

10.1021/jo402174v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by sigma-bond metathesis.

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收藏

页码：12154 / 12160

页数：7

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