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

• Grant number: 11/19954-9
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: January 01, 2012
• End date: December 31, 2012
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Paula Gabriela Guimarães de Andrade
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

The palladium-catalyzed reactions are a powerful tool for the formation of C-C bonds. The hydroarylation of alkynes are 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.