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Synthesis of naphthyl-substituted terminal olefins via Pd-Catalyzed one-pot coupling of acetylnaphthalene, N-Tosylhydrazide with aryl halide

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Abstract In this study, a one-pot two-step Pd-catalyzed reductive eliminate between acetyl naphthalene derivatives, tosylhydrazide, and aryl halide, affording substituted 1(or 2)-(1-phenylvinyl)naphthalene in moderate-to-excellent yields, was reported. Notably, solvent played… Click to show full abstract

Abstract In this study, a one-pot two-step Pd-catalyzed reductive eliminate between acetyl naphthalene derivatives, tosylhydrazide, and aryl halide, affording substituted 1(or 2)-(1-phenylvinyl)naphthalene in moderate-to-excellent yields, was reported. Notably, solvent played a crucial role in the coupling of 1-acetyl naphthalene derivatives (toluene) or 2-acetyl naphthalene derivatives (1, 4-dioxane) as starting materials. Meanwhile, the scope of this one-pot coupling reaction was extended to 1(or 2)-naphthaldehyde substrates. Importantly, the catalytic system can be employed on a wide variety of substrates with good functional group tolerance. This protocol could also be particularly useful for the synthesis of olefins-substituents hydroxyl compounds.

Keywords: pot; tosylhydrazide aryl; aryl halide; one pot; pot coupling

Journal Title: Tetrahedron
Year Published: 2017

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