Sebastien Thibaudeau, from the University of Poitiers, will deliver a seminar entitled, "Polycationic Superelectrophiles: Ideal Intermediates for Molecular Diversity." Hosted by Keith Woerpel.
For more information on Sebastien Thibaudeau, click here.
Abstract: The strategic and practical role of organic synthesis is critical to the success of discovering and developing new drugs. A general consensus has now emerged that library size is not everything; library diversity, in terms of molecular structure and thus function, is crucial.1
In superacid,2 such as HF/SbF5, functionalized organic molecules can be (poly)protonated to furnish electrophilic species which can react with very poor nucleophiles. This superelectrophilic activation3 can thus be applied to the development of unprecedented organic reactions.
Through the use of ammonium-carbenium,4 keteniminium,5 ammonium-oxonium6 or other modes of superelectrophilic activation,7,8 original fluorinated building blocks and bioactive compounds can be efficiently synthesized, opening new possibilities for the direct and effective preparation of (fluorinated) elaborated compounds of high synthetic and biological values.
1) D. G. Brown, J. Boström, J. Med. Chem. 2016, 59, 4443
2) G. A. Olah, G. K. S. Prakash, A. Molnar, J. Sommer, Superacid chemistry, 2nd Edition John Wiley and Sons; New York, 2009.
3) G. A. Olah, D. Klumpp, Superelectrophiles and their chemistry, John Wiley and Sons; New York, 2008.
4) (a) S. Thibaudeau, A. Martin-Mingot, M-P. Jouannetaud, O. Karam, F. Zunino, Chem. Commun. 2007, 3198; (b) G. Compain, A. Martin-Mingot, G. Frapper, C. Bachmann, M-P. Jouannetaud, S. Thibaudeau, Chem. Commun. 2012, 48, 5877.
5) (a) B. Theunissen, B. Métayer, N. Henry, G. Compain, J. Marrot, A. Martin-Mingot, S. Thibaudeau, G. Evano, J. Am. Chem. Soc. 2014, 136, 12528. (b) B. Métayer, G. Compain, K. Jouvin, A. Martin-Mingot, C. Bachmann, J. Marrot, G. Evano, S. Thibaudeau, J. Org. Chem. 2015, 80, 3397.
6) N. Probst, A. Martin, J. Désiré, A. Mingot, J. Marrot, Y. Blériot, S. Thibaudeau, Org. Lett. 2017, 19, 1040.
7) L. J. C. Bonazaba Milandou, H. Carreyre, S. Alazet, G. Greco, A. Martin-Mingot, C. Nkounkou Loumpangou, J-M. Oumaba, F. Bouazza, T. Billard, S. Thibaudeau, Angew. Chem. Int. Ed. 2017, 56, 169.
A. Martin, A. Arda, J. Désiré, A. Martin-Mingot, N. Probst, P. Sinaÿ, J. Jiménez-Barbero, S. Thibaudeau, Y. Blériot, Nat. Chem. 2016, 8, 186.