Boron(III)-Catalyzed C2-Selective C-H Borylation of Heteroarenes

被引：34

作者：

Zhong, Qi ^{[1
]}

Qin, Shengxiang ^{[1
]}

Yin, Youzhi ^{[1
]}

Hu, Jiajun ^{[1
]}

Zhang, Hua ^{[1
]}

机构：

[1] Nanchang Univ, Coll Chem, 999 Xuefu Ave, Nanchang 330031, Jiangxi, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 45期

基金：

中国国家自然科学基金;

关键词：

boron; heteroarenes; homogeneous catalysis; reaction mechanisms; synthetic methods; CATALYZED BORYLATION; ELECTROPHILIC BORYLATION; BOND ACTIVATION; DIRECT BORANE; LEWIS-ACID; ARENE; FUNCTIONALIZATION; REACTIVITY; BORENIUM; COMPLEXES;

D O I：

10.1002/anie.201808590

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A BF3Et2O-catalyzed C2-selective C-H borylation of indoles with bis(pinacolato)diboron was developed to afford indole-2-boronic acid pinacol esters. A variety of functional groups were tolerated, and other heteroarenes like pyrrole and benzo[b]thiophene were also suitable substrates. An electrophilic substitution mechanism was proposed based on the preliminary mechanistic studies. This novel transformation utilizes simple and cheap BF3Et2O as catalyst and exhibits unusual C2 regioselectivity, providing a significant non-transition-metal-catalyzed C-H borylation and an efficient method towards the synthesis of C2-functionalized heteroarenes.

引用

页码：14891 / 14895

页数：5

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