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Chemistry Seminar - Glenn M. Sammis

Posted on 2017-08-14 in Events
Aug 15, 2017



Title:

Target-Inspired Radical Methodology Development

The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorine-containing 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 a transition metal-free methodology that marks the first example of the direct and selective photochemical formation of C-F bonds3, a photocatalytic method utilizing Ru(bpy)32+,4 and xenon difluoride mediated method (Fig. 1).5 These approaches work well for a broad range of alpha-aryloxy substrates using very mild and inexpensive reaction conditions. The details of this work, along new radical synthetic methodology for C-C bond formation, will be discussed.

Fig. 1: Syntheses of Trifluoromethoxy Arenes Using Xenon Difluoride

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. Chatalova Sazepin, C.; Binayeva, M.; Epifanov, M.; Zhang, W.; Foth, P.; Amador, C.; Jagdeo, M.; Boswell, B.; Sammis, G. M. Org. Lett., 2016, 18, 4570-4573.

Date: Tuesday, August 15, 2017

Time: 11:00 a.m.

Place: Thorvaldson 205A EVERYONE WELCOME

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