Base-Promoted Formal [4+3] Annulation between 2-Fluorophenylacetylenes and Ketones: A Route to Benzoxepines

被引：32

作者：

Ouyang, Lu ^{[1
]}

Qi, Chaorong ^{[1
]}

He, Haitao ^{[1
]}

Peng, Youbin ^{[1
]}

Xiong, Wenfang ^{[1
]}

Ren, Yanwei ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 03期

基金：

中国国家自然科学基金;

关键词：

STEREOSELECTIVE ALPHA-VINYLATION; CATALYZED 5+2 ANNULATION; SYNTHETIC APPROACH; HELIANTHUS-ANNUUS; HYDROXY KETONES; GAMMA-LACTONES; ARYLACETYLENES; ACIDS; FUNCTIONALIZATION; ALKENES;

D O I：

10.1021/acs.joc.5b02487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first base-promoted formal [4 + 3] annulation between 2-fluorophenylacetylenes and ketones has been disclosed. The reaction proceeds through a tandem alpha-vinylation of ketones followed by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of the in situ generated beta,gamma-unsaturated ketone intermediates, providing a straightforward access to a wide range of functionalized benzoxepines in moderate to high yields. The transition-metal-free methodology featured a wide substrate scope, the use of easily available starting materials, and a high functional group tolerance.

引用

页码：912 / 919

页数：8

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