Amination of redox-active esters of fluorinated alicyclic carboxylic acids with diazirines

The objective of this research program is the development of new green synthetic methods with emphasis on metal-free procedures for the simple preparation of biologically and commercially important molecules. In particular, fluorinated sp3-enriched Nitrogen-containing compounds will be prepared by radical reactions of redox-active esters (i.e., N-hydroxyphthalimide, N-hydroxy-2-thiopyridone, etc.) derived from fluorinated alicyclic carboxylic acids with the diazirine derivatives.
According to this, we are going to establish reactivity patterns for the redox-active esters derived from fluorinated alicyclic carboxylic acids in the reaction with diazirines. Then find optimal reaction conditions for this transformation, providing either imine or diazirine products selectively and demonstarate possible applications of the products obtained for the synthesis of potentially useful fluorinated Nitrogen-containing compounds, e.g., amines, hydrazines, or nitrogen-containing heterocycles.

Faculty Supervisor:

Thierry Ollevier

Student:

Partner:

Taras Shevchenko National University of Kyiv

Discipline:

Life Sciences

Sector:

Pharmaceuticals; Sustainability & the Environment; Other

University:

Université Laval

Program: