Glenn Sammis
Glenn Sammis
Tue, Nov. 6, 2018, 4:30pm
Edward C Taylor Auditorium, Frick B02
Host: Erik Sorensen
New Strategies and Reagents for Fluorination
The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorinecontaining pharmaceuticals. Traditional methods potentially applicable to drug synthesis rely on the use of ionic forms of fluorine (F– or F+). We have demonstrated that the electrophilic fluorine sources N-fluorobenzenesulfonimide (NFSI)1 and Selectfluor®1 can effectively fluorinate alkyl radicals.2 Continuing research towards utilizing these fluorine atom transfer reagents in synthesis, we have recently developed new methods for the selective photochemical formation of C-F bonds,3,4,5 and a new XeF2 method for the synthesis of trifluoromethoxy arenes.6 New advances in radical fluorination, along with the development of new one-pot fluoroalkylations (Scheme 1), will be discussed.
References:
1. M. Rueda-Becerril, C. Chatalova Sazepin, J. C. T. Leung, T. Okbinoglu, P.
Kennepohl, J. -F. Paquin, G. M. Sammis, G. M. J. Am. Chem. Soc. 2012, 134, 4026-
4029.
2. For other early examples of fluorine transfer using Selectfluor®, see: a) Yin, F.;
Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401. b) Barker, T. J.; Boger,
D. L. J. Am. Chem. Soc. 2012, 134, 13588. c) Liu, W.; Huang, X.; Cheng, M.-J.;
Nielsen, R. J.; Goddard III, W. A.; Groves, J. T. Science 2012, 337, 1322. d) Bloom,
S.; Pitts, C. R.; Miller, D. C.; Haselton, N.; Holl, M. G.; Urheim, E.; Lectka, T. Angew.
Chem. Int. Ed. 2012, 51, 10580.
3. Leung, J. C. T.; Chatalova-Sazepin, C.; West, J.; Rueda-Becerril, M.; Paquin, J. –
F.; Sammis, G. M. Angew. Chem. Int. Ed. 2012, 51, 10804.
4. M. Rueda-Becerril, O. Mahé, M. Drouin, M. B. Majewsky, J. G. West, M. O. Wolf,
G. M. Sammis, J.-F. Paquin J. Am. Chem. Soc. 2013, 136, 2637.
5. Leung, J. C. T.; Sammis, G. M., Eur. J. Org. Chem., 2015, 2015, 2197.
6. Chatalova Sazepin, C.; Binayeva, M.; Epifanov, M.; Zhang, W.; Foth, P.; Amador,
C.; Jagdeo, M.; Boswell, B.; Sammis, G. M. Org. Lett., 2016, 18, 4570.