[1,4]-Aza-Brook Rearrangement for Efficient Formation of Benzynes and Their Cycloaddition

被引：6

作者：

Huang, Ze-Ao ^{[1
,2
]}

Tang, Fan ^{[3
]}

Xu, Yan-Jun ^{[1
,2
]}

Lu, Chong-Dao ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zones, Urumqi 830011, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Urumqi 830011, Peoples R China

[3] Changji Univ, Dept Chem & Appl Chem, Changji 831100, Peoples R China

来源：

SYNLETT | 2015年 / 26卷 / 07期

基金：

中国国家自然科学基金;

关键词：

silyl migration; amines; aza-Brook rearrangement; benzyne; cycloaddition; ANION RELAY CHEMISTRY; CHROMIUM TRICARBONYL COMPLEXES; ASYMMETRIC-SYNTHESIS; BROOK REARRANGEMENT; ALPHA-SILYLAMINES; ONE-POT; SILICON; GENERATION; ALDIMINES; LINCHPIN;

D O I：

10.1055/s-0034-1380187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient benzyne cycloaddition triggered by an aza-Brook rearrangement is reported. In this reaction, 2-(trimethylsilyl)aryl triflates bearing a benzylic secondary amine group at the 3-position undergo base-promoted [1,4]-carbon-to-nitrogen silyl migration (aza-Brook rearrangement) to generate benzyne intermediates, which are then trapped by intermolecular or intramolecular cycloaddition involving 1,3-dienes or 1,3-dipoles. This procedure furnishes various cycloadducts in yields of up to 99%.

引用

页码：891 / 896

页数：6

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