Impact of Solvent and Their Contaminants on Pd/C Catalyzed Suzuki‐Miyaura Cross‐Coupling Reactions

• DOI: 10.1002/hlca.202100035
• Publication Date: 2021-04-20T00:57:07Z
• Authors: Alexandre de Lamb...; Christophe Allemann; Luca Fadini
• Keywords: Phenylboronic acid; Coupling reaction; Maleic anhydride; Solvent exposure

Abstract The aim of this work was to understand if solvent contaminants can interfere in Suzuki ’s cross‐coupling reactions and it explain the lack robustness industrial processes. For purpose, several parameters were tested on model reaction between 2‐bromonaphthalene phenylboronic acid catalyzed by Pd/C. Best results obtained using THF as solvent. Traces precursors used solvents, such 2,3‐dihydrofurane or maleic anhydride (100–300 ppm related solvent) strongly poisoned reaction, decreasing conversion significantly. This means that ensure robust production, quality must be analyzed at level. Fortunately, addition triphenylphosphine circumvent catalyst poisoning.