I-SITE 2018 - Junior - Smart C–H Bond Functionalization at s-Tetrazine for New materials and Medical Applications

In the last few years s-tetrazines have been the object of considerable interest in various research fields of primary importance. These include the development of functional materials for energy and health applications. For instance, tetrazines are bioorthogonal “Click Chemistry” reagents or useful fluorophores with original optoelectronic features. Yet, the synthetic preparation of highly functionalized s-tetrazine remains extremely limited. It mainly relies on the initial Pinner synthesis of poorly-functionalized tetrazine halides or arenes, showing serious synthetic limitations. This entire project aims at delivering the next generation of synthetic methods towards modular and convenient construction of highly functionalized tetrazines and useful derivatives. The potential of application is very significant, and overall is industrially-pertinent, as testified by the intense patenting in the field in the last years, including in our research group. We target metal-catalysed reactions based on modern sustainable chemistry and green processes, by mainly using ortho-selective C–H bond activation and direct C–H bond functionalization at s-tetrazines. We will investigate the methods and reaction scope of usable transition metals with electrophilic and nucleophilic reagents to integrate with tetrazine-core useful reactive functional groups through C–C and C–X bond formation (X = O, N, P, B, etc.). The complementary electrophilic and nucleophilic methodologies developed will then apply on targets which span various topical domains from molecular materials to medicinal applications. 

Principal investigator: Dr Julien Roger