Oxidative cycloaddition and cross-coupling processes on unactivated benzene derivatives

被引：68
|
作者：
Jacquemot, Guillaume [1 ]
Menard, Marc-Andre [1 ]
L'Homme, Chloe [1 ]
Canesi, Sylvain [1 ]
机构：
[1] Univ Quebec, Lab Methodol & Synth Prod Nat, Montreal, PQ H3G 3P8, Canada
来源：
CHEMICAL SCIENCE | 2013年 / 4卷 / 03期
基金：
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词：
FORMAL 2+3 CYCLOADDITION; HYPERVALENT IODINE REAGENTS; PINACOL TANDEM PROCESS; DIELS-ALDER REACTION; C-H ACTIVATION; PHENOL DEAROMATIZATION; SUBSTITUTED PHENOLS; DIRECT ARYLATION; AMIDATION; RING;
D O I：
10.1039/c2sc22318j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Treatment of phenols or anilines containing a sulfonyl group in the presence of a hypervalent iodine reagent promotes a formal dearomatizing [2 + 3] cycloaddition reaction on unactivated benzene and naphthalene derivatives. This process occurs via an intramolecular nucleophilic addition to the Wheland species generated during the oxidative activation. Subsequent treatment under acidic conditions readily transforms the tricyclic system into a biaryl via a formal cross-coupling process.
引用
收藏
页码：1287 / 1292
页数：6
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