4.8 Article

Cobalt(I)-Catalyzed (3+2+2) Cycloaddition between Alkylidenecyclopropanes, Alkynes, and Alkenes

Journal

ORGANIC LETTERS
Volume 25, Issue 46, Pages 8372-8376

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c03511

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This study investigates the application of cobalt(I) catalysts with bisphosphine ligands for promoting intramolecular cycloadditions of enynylidenecyclopropanes. The method successfully synthesizes 5,7,5-fused tricyclic systems with high yields and complete diastereo- and chemoselectivity. Interestingly, the scope and mechanism of this reaction differ from previously reported annulations using rhodium and palladium catalysts.
Cobalt(I) catalysts equipped with bisphosphine ligands can be used to promote formal (3 + 2 + 2) intramolecular cycloadditions of enynylidenecyclopropanes of type 1. The method provides synthetically appealing 5,7,5-fused tricyclic systems in good yields and with complete diastereo- and chemoselectivity. Interestingly, its scope differs from that of previously reported annulations based on precious metal catalysts, specifically rhodium and palladium. Noticeably, density functional theory calculations confirm that the mechanism of the reaction is also different from those proposed for these other catalysts.

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