Issue 22, 2023

Construction of polysubstituted pentafulvenes via palladium-catalyzed deacetylation of enones

Abstract

Herein, we report an efficient synthetic method for polysubstituted pentafulvenes via palladium-catalyzed deacetylative [2+2+1] annulation of enones with alkynes. Aryl-, alkenyl-, and alkyl-substituted α,β-enones were suitable substrates, affording the pentafulvene products in moderate to good yields. This protocol shows excellent compatibility with sensitive halides, free hydroxyl groups, and heterocycles. One-pot gram-scale synthesis and further applications in the late-stage modification of natural products demonstrate the synthetic utility of this method.

Graphical abstract: Construction of polysubstituted pentafulvenes via palladium-catalyzed deacetylation of enones

Supplementary files

Article information

Article type
Communication
Submitted
06 Dec 2022
Accepted
13 Feb 2023
First published
14 Feb 2023

Chem. Commun., 2023,59, 3269-3272

Construction of polysubstituted pentafulvenes via palladium-catalyzed deacetylation of enones

L. Li, X. Wang, H. Xu and H. Dai, Chem. Commun., 2023, 59, 3269 DOI: 10.1039/D2CC06644K

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