Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones

Jia-Cheng Li , Tian-Qi Hu , Zhou Xu , Bo Zhou , Long-Wu Ye
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Abstract

The one-carbon ring expansion of benzocyclobutenones is an efficient methodology for the assembly of cyclic ketones. However, hazardous reagents or noble metal catalysts are frequently required. Herein, we disclose a copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones, allowing the practical and atom-economical construction of diverse pyrryl 1-indanones in generally good yields under mild reaction conditions. This reaction represents an important advancement in the ring expansion of benzocyclobutenones via vinyl cation pathway.

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铜催化 1,5-二炔与苯并环丁烯酮的分子间正规 [4 + 1] 环化反应
苯并环丁烯酮的一碳环扩展是组装环酮的有效方法。然而,这种方法经常需要使用危险试剂或贵金属催化剂。在此,我们揭示了一种铜催化的 1,5- 二炔与苯并环丁烯酮的分子间形式 [4 + 1] 环化反应,从而可以在温和的反应条件下,以普遍较好的产率,构建出实用且原子经济的各种吡咯 1-茚酮。该反应是苯并环丁烯酮通过乙烯基阳离子途径扩环的重要进展。
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来源期刊
Tetrahedron chem
Tetrahedron chem Organic Chemistry
CiteScore
3.60
自引率
0.00%
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0
审稿时长
27 days
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