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

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.

Keywords

• Ring expansion
• [4 + 1] annulation
• Benzocyclobutenones
• Diynes
• Copper catalysis