Palladium‐Catalyzed Regioselective peri ‐ and ortho ‐Halogenation of 1‐Naphthaldehydes: Application to the Synthesis of Polycyclic Natural Product Skeletons - Unité de Chimie et Procédés (UCP)
Article Dans Une Revue European Journal of Organic Chemistry Année : 2023

Palladium‐Catalyzed Regioselective peri ‐ and ortho ‐Halogenation of 1‐Naphthaldehydes: Application to the Synthesis of Polycyclic Natural Product Skeletons

Résumé

Herein, a regioselective bromination or chlorination reaction of 1‐naphthaldehydes is described. Without additive, the palladium‐catalyzed C−H halogenation showed a C8‐regioselectivity, whereas the formation of an aromatic imine intermediate allowed a switch to a C2‐reactivity. Mechanistic studies and DFT calculations were performed to explain the regioselectivity and the synthesized halogenated products were used as key building blocks to access polycyclic natural product skeletons.
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Dates et versions

hal-04202304 , version 1 (11-09-2023)

Identifiants

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Hugo Amistadi-Revol, Julian Garrec, Nicolas Casaretto, Sébastien Prévost. Palladium‐Catalyzed Regioselective peri ‐ and ortho ‐Halogenation of 1‐Naphthaldehydes: Application to the Synthesis of Polycyclic Natural Product Skeletons. European Journal of Organic Chemistry, 2023, 26 (24), ⟨10.1002/ejoc.202300359⟩. ⟨hal-04202304⟩
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