Hydroarylation reaction studies of alkynes catalyzed by palladium using diazonium salts: application in the synthesis of combretastatines analogues

Abstract

The palladium-catalyzed reactions are a powerful tool for the formation of C-C bonds. The hydroarylation of alkynes is part of the synthetic arsenal and has increased interest in recent years. In this context, we propose the methodological study of the hydroarylation reaction of alkynes employing diazonium salts catalyzed by palladium. The reaction model to be investigated will be between dimethyl acetylenedicarboxylate and tetrafluoroborate p-methoxy phenyl diazonium. Variables will be studied as a solvent, temperature, source of palladium, stoichiometry between olefin and diazonium salt, and acidity of the reaction medium in order to establish the best condition in terms of yields and selectivity. The alkenes obtained will be applied in the synthesis of combretastatinas analogues, composed of tubulin promising inhibitory activity in several types of Cancer.(AU)