EXPLORATION OF SYNTHETIC METHODOLOGIES FOR SUSTAINABLE AND EFFICIENT ORGANIC TRANSFORMATIONS

DURING THE LAST DECADES, NEW SYNTHETIC METHODOLOGIES AND TOOLS WERE DEVELOPED TO INCREASE THE EFFICIENCY OF ORGANIC REACTIONS IN TERMS OF SELECTIVITY, PRODUCTIVITY AND SUSTAINABILITY. ESPECIALLY ABOUT SUSTAINABILITY, NOWADAYS IT IS CRUCIAL TO PAY ATTENTION TO GREEN CHEMISTRY AND ITS PRINCIPLES IN THE SET-UP OF A REACTION. AMONG ORGANIC TRANSFORMATIONS, THE OXIDATION AND REDUCTION OF ORGANIC MOLECULES REPRESENT VERY STRAIGHTFORWARD PROCEDURES IN ORGANIC SYNTHESIS TO PREPARE DIFFERENTLY FUNCTIONALIZED COMPOUNDS. UNFORTUNATELY, MOST OXIDATIVE AND REDUCTIVE PROTOCOLS SUFFER FROM LOW SELECTIVITY AND BAD SUSTAINABILITY INVOLVING THE GENERATION OF HUGE AMOUNTS OF WASTE. IN THIS CONTEXT, SEVERAL MODERN TOOLS TO CARRY ON ORGANIC TRANSFORMATIONS ARE BECOMING WIDESPREAD, AMONG THEM, FLOW CHEMISTRY HAS EMERGED AS A VERY POWERFUL TECHNIQUE FOR MAKING ORGANIC REACTIONS THANKS TO ITS PECULIAR FEATURES: IMPROVED HEAT AND MASS TRANSFER, BETTER SCALABILITY, INCREASED REACTION EFFICIENCY AND IMPROVED REPRODUCIBILITY LEADING TO HIGH-THROUGHPUT PROCESSES. IN THIS PHD PROJECT, NEW SUSTAINABLE AND EFFICIENT SYNTHETIC METHODOLOGIES FOR THE PREPARATION OF DIFFERENT HIGH-ADDED VALUE ORGANIC COMPOUNDS WERE DEVELOPED. SPECIFICALLY, A SUSTAINABLE AND STREAMLINED PROCESS FOR THE PREPARATION OF THE PHARMACEUTICAL INTERMEDIATE 8-CARBOXY-3-METHYLFLAVONE THROUGH AN ALKENE OXIDATIVE CLEAVAGE WERE PROPOSED IN COLLABORATION WITH RECORDATI S.P.A. PAYING PARTICULAR ATTENTION TO SUSTAINABILITY ASPECTS EVEN BY LEVERAGING TOOLS LIKE FLOW CHEMISTRY. THEN, A SECOND GOAL WAS CENTERED ON THE DEVELOPMENT OF NEW MACROCYCLIC SYSTEMS APPLIED IN THE FIELD OF REDUCTION REACTIONS. IN PARTICULAR, THE APPLICATION OF A NOVEL TRIAZOLE-BORANE COMPLEX BASED ON AZAMACROCYCLIC SCAFFOLDS IN THE REDUCTION OF CARBONYL COMPOUNDS WILL BE DISCUSSED. FINALLY, NEW CONTINUOUS-FLOW PLATFORMS FOR THE HANDLING OF N-BUTYLLITHIUM SOLUTION IN LITHIUM-HALOGEN EXCHANGE REACTIONS WERE DEVELOPED UNDER THE SUPERVISION OF PROF. JEAN-CHRISTOPHE M. MONBALIU (UNIVERSITY OF LIÈGE) BRINGING TO THE SYNTHESIS OF SEVERAL ARYLKETONES WITH HIGH PRODUCTIVITY AND SELECTIVITY.