Frontiers in tetrazine derivatives functionalization: meta and para selective C-H activation – FIT-Fun
ANR JCJC FIT-Fun
Frontiers in Tetrazine derivatives Functionalization: <br />meta and para selective C–H activation
meta and para-functionnalisation of s-tetrazine
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 remain 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.
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.
New synthetic routes for metallacyles based on s-tetrazines, characterisations and mechanism understanding (by DFT calculations and by electrochemistry).
New applications and functionnalisation by oxydative coupling based on transition metals.
New s-tetrazines molecules: the applied targets span a large domain from molecular materials to bioactive drugs.
1- C. D. Mboyi, A. Daher, N. Khirzada, C. H. Devillers, H. Cattey, P. Fleurat-Lessard, J. Roger, J.-C. Hierso New J. Chem. 2020, 44, 15235–15243. (10.1039/D0NJ02338H)
2- C. D. Mboyi, D. Vivier, A. Daher, P. Fleurat-Lessard, H. Cattey, C. H. Devillers, C. Bernhard, F. Denat, J. Roger, J.-C. Hierso Angew. Chem. Int. Ed. 2020, 59, 1149–1154. (10.1002/anie.201911947)
hal.archives-ouvertes.fr/hal-02469034
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 remain 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.
Project coordination
Julien Roger (INSTITUT DE CHIMIE MOLECULAIRE DE L'UNIVERSITE DE BOURGOGNE)
The author of this summary is the project coordinator, who is responsible for the content of this summary. The ANR declines any responsibility as for its contents.
Partnership
ICMUB INSTITUT DE CHIMIE MOLECULAIRE DE L'UNIVERSITE DE BOURGOGNE
Help of the ANR 215,730 euros
Beginning and duration of the scientific project:
February 2019
- 48 Months
