Double Heteroatom Functionalization of Arenes Using Benzyne Three-Component Coupling

被引：79

作者：

Garcia-Lopez, Jose-Antonio ^{[1
]}

Cetin, Meliha ^{[1
]}

Greaney, Michael F. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

arynes; benzyne; Grignard reaction; heterocycles; multicomponent reactions; CATALYZED ELECTROPHILIC AMINATION; CONTINUOUS-FLOW SYNTHESIS; TRANSITION-METAL-FREE; ARYNES; INSERTION; REARRANGEMENT; EFFICIENT; ARYLATION; REAGENTS; BONDS;

D O I：

10.1002/anie.201410751

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl aryl-sulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2-difunctionalized arenes.

引用

页码：2156 / 2159

页数：4

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