Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles

Steven Frippiat (1) , Antoine Peresson (1) , Thibaut Perse (2) , Yvan Ramondenc (1) , Cédric Schneider (1) , Olivier Querolle (2) , Patrick Angibaud (2) , Virginie Poncelet (2) , Lieven Meerpoel (2) , Vincent Levacher (1) , Laurent Bischoff (1) , Christine Baudequin (1) , Christophe Hoarau (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Janssen Research & Development

The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles as well as innovative C2- and C5-arylated fused imidazoles tricycles with a five- to seven-membered middle ring.

Keywords: Alkenylation; Arylation; C-H Functionalisation; Palladium catalysis; Imidazole; catalysis; arylation; palladium; heterocycles; alkenation; C-H functionalization; palladium catalysis; imidazole; alkenylation C-H functionalization; alkenylation

Domains: Chemical Sciences

Steven Frippiat, Antoine Peresson, Thibaut Perse, Yvan Ramondenc, Cédric Schneider, et al.. Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles. SYNLETT, 2020, 31 (10), pp.1015-2021. ⟨10.1055/s-0040-1708003⟩. ⟨hal-02548986⟩