Aryne-mediated [2,3]-sigmatropic rearrangement of tertiary 2,3-allenylamines bearing an electron-withdrawing group at the α-position

被引：3
作者：
Han, Lu [1 ,2 ]
Zhang, Xue-Ting [1 ,2 ]
Xie, Dong [1 ,2 ]
Tian, Shi-Kai [1 ,2 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Ctr Excellence Mol Synth CAS, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 24期
基金：
中国国家自然科学基金;
关键词：
GENERATED METAL CARBENOIDS; AMINO-ACID DERIVATIVES; AMMONIUM YLIDES; STEREOSELECTIVE-SYNTHESIS; INTRAMOLECULAR REACTION; STEVENS REARRANGEMENT; CATALYZED-REACTIONS; CONCISE SYNTHESIS; BENZYNE; ACCESS;
D O I：
10.1039/d1ob00887k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented [2,3]-sigmatropic rearrangement reaction of quaternary 2,3-allenylammonium ylides, generated in situ from tertiary 2,3-allenylamines and arynes, has been established. With 2-(trimethylsilyl)aryl triflates as aryne precursors, a range of tertiary 2,3-allenylamines bearing an electron-withdrawing group at the alpha-position smoothly participated in the aryne-mediated [2,3]-sigmatropic rearrangement at room temperature, delivering structurally diverse 2-vinylallyamines or 1-amino-1,3-dienes in moderate to excellent yields. The reaction proceeds in the absence of strong bases and transition metals, is compatible with moisture and air, and tolerates a wide variety of functional groups.
引用
收藏
页码：5353 / 5357
页数：5
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