Palladium-Catalyzed Regioselective peri- and ortho-Halogenation of 1-Naphthaldehydes: Application to the Synthesis of Polycyclic Natural Product Skeletons |
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Authors: | Hugo Amistadi-Revol Dr Julian Garrec Dr Nicolas Casaretto Dr Sébastien Prévost |
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Institution: | 1. Laboratoire de Synthèse Organique (LSO – UMR 7652), CNRS, Ecole Polytechnique, ENSTA Paris, Institut Polytechnique de Paris, 91120 Palaiseau, France;2. Unité Chimie et Procédés (UCP) ENSTA Paris, Institut Polytechnique de Paris, 91120 Palaiseau, France;3. Laboratoire de Chimie Moléculaire (LCM – UMR 9168), CNRS, Ecole Polytechnique, Institut Polytechnique de Paris, 91120 Palaiseau, France |
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Abstract: | 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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Keywords: | C−H activation 1-naphthaldehyde halogenation polycyclic natural products palladium catalysis |
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