Details

Autor(en) / Beteiligte

• Ouyang, Lu
• Qi, Chaorong
• He, Haitao
• Peng, Youbin
• Xiong, Wenfang
• Ren, Yanwei
• Jiang, Huanfeng

Titel

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

Ist Teil von

• Journal of organic chemistry, 2016-02, Vol.81 (3), p.912-919

Ort / Verlag

United States

Erscheinungsjahr

2016

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The first base-promoted formal [4 + 3] annulation between 2-fluorophenylacetylenes and ketones has been disclosed. The reaction proceeds through a tandem α-vinylation of ketones followed by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of the in situ generated β,γ-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.