One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts

被引：73
|
作者：
Reitti, Marcus [1 ]
Villo, Piret [1 ]
Olofsson, Berit [1 ]
机构：
[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 31期
基金：
瑞典研究理事会;
关键词：
arylation; density functional calculations; hypervalent compounds; oxidation; reaction mechanisms; HYPERVALENT IODINE COMPOUNDS; M-CHLOROPERBENZOIC ACID; TRANSITION-METAL-FREE; FREE N-ARYLATION; UNSYMMETRICAL LAMBDA(3)-IODANES; ARYLBORONIC ACIDS; IPSO-NITRATION; MILD SYNTHESIS; ARYL IODIDES; REAGENTS;
D O I：
10.1002/anie.201603175
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryl-iodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.
引用
收藏
页码：8928 / 8932
页数：5
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