Pd-Catalyzed Regioselective Decarboxylative/C–H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers

Jean-Baptiste Rouchet (1) , M. Hachem , Cédric Schneider (1) , Christophe Hoarau (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

A direct introduction of vinyl ethers into C–H bond of heterocycles is reported. For this purpose, decarboxylative direct C–H cross-coupling of 1,3-diazoles with α-carboxyvinyl ethers as coupling partners was achieved under Pd(0)/Cu(I) cooperative catalysis to produce various α-heteroarylated vinylethers. This methodology was applied to the innovative production of heteroarylated enolizable ketones and naturally occurring bis-oxa(thia)zoles.

Mots clés: Azoles; α-alkoxyalkenylation; Enol ether; Decarboxylative cross-coupling; α-carboxyvinylethers; C−H functionalization; Pd-catalysis

Domaines: Chimie

Jean-Baptiste Rouchet, M. Hachem, Cédric Schneider, Christophe Hoarau. Pd-Catalyzed Regioselective Decarboxylative/C–H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers. ACS Catalysis, 2017, 7 (8), pp.5363-5369. ⟨10.1021/acscatal.7b01330⟩. ⟨hal-02046307⟩