Base-Promoted Decarboxylative Annulation of Methyl 2-(2-Bromophenyl)acetates and Ynones to Access Benzoxepines

被引：3
|
作者：
Chen, Lu-Lu [1 ]
Li, Feng [1 ]
Yang, Qing [1 ]
Ye, Ya-Fang [1 ]
Yang, Wan-Wan [1 ]
Wang, Yan-Bo [1 ]
机构：
[1] Henan Univ, Coll Chem & Chem Engn, Henan Engn Res Ctr Funct Mat & Catalyt React, Kaifeng 475004, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 05期
基金：
中国国家自然科学基金;
关键词：
VINYLETHYLENE CARBONATES; CONSTRUCTION; FACILE;
D O I：
10.1021/acs.joc.2c02870
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient base-mediated decarboxylative annulation of ynones with methyl 2-(2-bromophenyl)acetates has been developed. A broad range of benzoxepines were prepared with a broad substrate scope and high regioselectivity in moderate to excellent yields under transition-metal-free conditions. This method proceeds through a tandem [2 + 4] annulation, ring opening decarboxylative reaction, and the intramolecular nucleophilic aromatic substitution reaction. Additionally, the key intermediates were successfully obtained and characterized unambiguously by single-crystal X-ray crystallography, which could favorably support a decarboxylative annulation mechanism. Furthermore, gram-scale reaction and synthetic applications for the further functionalization are also studied.
引用
收藏
页码：3079 / 3088
页数：10
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