TripIod · Development of Triptycene-Based New Hypervalent Iodine Reagents for Selective Organic Synthesis

The challenge of achieving high selectivities (chemo/regio/stereoselectivity) in organic transformations is still very high. Selectivities are achieved through either covalent interactions involving metals or non-covalent interactions such as hydrogen bonding, halogen bonding or ion pairing involving organocatalysts or enzyme catalysts. Triptycenes are highly promising structures due to their rigidity, internal free volume, electron rich cavities, three aromatic rings opened for π-stacking interactions and the possibility of atropisomerism. We want to exploit their potential of non-covalent interactions in chemo-, regio- and stereoselective reactions by using triptycene scaffolds for the synthesis of iodine-based reagents. The proposed research will focus in utilization of internal free volume for selectivity in reactions to explore selectivity through π-interaction. This process will open up new directions by focusing on the following objectives: (a) synthesis of different iodotriptycenes; (b) oxidation of iodotriptycene to iodine(III) derivatives including polymer-based reagents; (c) development of chiral triptycene-based iodine(III) derivatives; (d) application of the methodology in the flow synthesis of target molecules and (e) training through research and career development of incoming post-doctoral fellow. The proposed methodology has the capacity to make a sound impact on the scientific community, and to change existing protocols in industry. The MSC Fellowship will provide the post-doctoral fellow to strengthen scientific knowledge and enrich skills, innovative ideas, managing skills and to establish himself as an international scientist.