Scalable and efficient approaches towards the synthesis of cis- and trans-1,3-disubstituted mono-, di- and trifluoromethylcyclobutane building blocks are disclosed. Effects of the fluoroalkyl substituents and other structural featur...
Artikel
Palladium‐Catalyzed Regioselective peri‐ and ortho‐Halogenation of 1‐Naphthaldehydes: Application to the Synthesis of Polycyclic Natural Product Skeletons
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A palladium-catalyzed regioselective halogenation reaction of 1-naphthaldehydes was disclosed. When aldehyde was used as directing group, a C8-selectivity was observed whereas an imine formation was necessary to achieve C2-halogenation. The mechanism as well as the regioselectivity of the reaction were studied and the halogenated products were used in the synthesis of natural product skeletons.
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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