ANR 2018 - JCJC - Fit-Fun - Frontiers in Tetrazine derivatives Functionalization: meta and para selective C–H activation

In the last few years, s-tetrazines have been the object of considerable interest in various fields, which spread out from energetic materials to biomedicine. Despite this significant extent of applications, the synthetic preparation modes of functionalized s-tetrazine remains very limited. They mainly rely on the initial Pinner synthesis of prefunctionalized tetrazine core with serious steric and electronic limitations. The present project aims now at providing new selectivities in C–H activation of s-aryltetrazine core by extending the methods and scope of utilizable transition metals to meta- and para- remote C–H functionalization with electrophilic and nucleophilic reagents: the applied targets span a large domain from molecular materials to bioactive drugs. In-depth mechanistic study will be achieved by analytical electrochemistry and DFT studies, in order to solve the issue of rate limiting step (OA, RE, TM) and reagents compatibility in the reaction process.

Principal investigator: Dr Julien ROGER