Selective C3- or C5-Borylation of furfural derivatives: Enabling the synthesis of tri- and tetra-substituted furan Analogues - Archive ouverte HAL Access content directly
Journal Articles Tetrahedron Chem Year : 2024

Selective C3- or C5-Borylation of furfural derivatives: Enabling the synthesis of tri- and tetra-substituted furan Analogues

Abstract

A strategy of C3/C4 and C5/C4 bis-C–H functionalization of furfural and 5-hydroxymethylfurfural is presented. This task has been accomplished by the initial iridium-catalyzed C–H borylation of furfural, equipped with an appropriate imine function. Depending on the nature of the ligand employed, the borylation takes place selectively at C3 or C5, the products serving in turn as partners in Suzuki-Miyaura cross-couplings. After aldehyde function regeneration, some of the resulting heterobiaryl compounds underwent a, C3- or C5-directed, C4-selective Pd-catalyzed Fujiwara-Moritani olefination. These hitherto unknown serial C3/C4 and C5/C4 bis C–H functionalization strategies allow the straightforward conversion of the bio-sourced platform molecules furfural and 5-hydroxymethylfurfural into tri- and tetra-substituted furaldehyde derivatives.
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hal-04617994 , version 1 (19-06-2024)

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Alessia Mori, Mariana Isabel Crespo Monteiro, Filipa Siopa, Giovanni Poli, Julie Oble. Selective C3- or C5-Borylation of furfural derivatives: Enabling the synthesis of tri- and tetra-substituted furan Analogues. Tetrahedron Chem, 2024, 11, pp.100079. ⟨10.1016/j.tchem.2024.100079⟩. ⟨hal-04617994⟩
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