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

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

doi:10.1055/s-0040-1708003

Journal articles

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

Abstract : 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

Document type :

Journal articles

Domain :

Chemical Sciences

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https://hal-normandie-univ.archives-ouvertes.fr/hal-02548986
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Submitted on : Tuesday, December 1, 2020 - 2:28:22 PM
Last modification on : Monday, December 7, 2020 - 1:29:01 PM

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