Article Dans Une Revue Tetrahedron Letters Année : 2025

Palladium-catalyzed selective C5-H bond arylation of pyrazole using hydroxymethyl substituent as blocking group

Résumé

In this study, we investigated the reactivity of two unprotected hydroxymethyl-substituted pyrazoles in palladium-catalyzed C-H arylation. The conditions for the regioselective C5-arylation of (1-methylpyrazol-4-yl) methanol, while leaving the hydroxymethyl function intact, have been established. The reaction demonstrates broad substrate compatibility, accommodating a diverse array of electron-deficient and electron-excessive aryl bromides, including those bearing substituents in the para-, meta- and ortho-positions and is compatible with heteroaryl bromides. Furthermore, the reaction uses only 2 mol% of an air-stable palladium catalyst and KOPiv as an inexpensive base. This method enables the synthesis of a diverse range of pyrazole derivatives in a single step, thus facilitating the straightforward modification of their biological properties.

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Chimie
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hal-04929038 , version 1 (04-02-2025)

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Rabeb Ben Romdhane, Ridha Ben Salem, Henri Doucet. Palladium-catalyzed selective C5-H bond arylation of pyrazole using hydroxymethyl substituent as blocking group. Tetrahedron Letters, 2025, 157, pp.155465. ⟨10.1016/j.tetlet.2025.155465⟩. ⟨hal-04929038⟩
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