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Napredni reagenti za (asimetrično) nukleofilno fluoriranje|

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Oznaka in naziv projekta

N1-0185 Napredni reagenti za (asimetrično) nukleofilno fluoriranje
N1-0185 Advanced reagents for (asymmetric) nucleophilic fluorination

Logotipi ARRS in drugih sofinancerjev

© Javna agencija za raziskovalno dejavnost Republike Slovenije

Projektna skupina

Vodja projekta: doc. dr. Gašper Tavčar

dr. Melita Tramšek

Sodelujoče raziskovalne organizacije: Povezava na SICRIS

Sestava projektne skupine: Povezava na SICRIS

Vsebinski opis projekta

Although the proposed research represents homogeneous subject, devoted to the development of novel nucleophilic fluorination reagents and their application to selected classes of substrates, it can be divided into individual WP’s, connected closely together. Thus, WP1 will concentrate on the synthesis of sterically hindered imidazolium salts and imidazoles, either fluorinated on C2 of the heterocyclic ring or having fluoride or polyhydrogenpolyfluoride anion; WP2 will synthesize various variants of fluorinated pentacoordinated silicon species with the emphasis on alkyldiaryldifluorosilicates and various cations included imidazolium salts developed in WP1; WP3 devoted to the synthesis of asymmetric variants of reagents synthesized in WP1 and WP2 with the emphasis on the develoment of new chiral group, [2.2]paracyclophan-4-yl modified with alkyl substituents in position 5; WP4, where reagents prepared in WP’s 1-3 will be tested both on model compounds and pharmaceutically interesting substances; and, finally, WP5, which will be devoted to environmental aspects of the project including recycle of the spent reagents or their potential applications in catalytic amounts in connection with cheap fluorinating reagents. The details of individual WP’s are given below.

Osnovni podatki sofinanciranja so dostopni na spletni strani SICRIS.

Faze projekta in opis njihove realizacije (ang)

WP1 Development of imidazolium based nucleophilic fluorinating reagents

WP2 Development of hypervalent silicon based nucleophilic fluorinating reagents

WP3 Development of chiral nucleophilic fluorinating reagents

WP4 Reactivity of prepared nucleophilic fluorinating reagents in organic chemistry

WP5 Evaluation of economic and environmental potential of new reagents for use on industrially relevant systems

Bibliografske reference

  • Reference - SICRIS

  • 1. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319.

  • Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem. Int. Ed. 2013, 52, 8214-8264.

  • Mei, H.; Han, J.; Fustero, S.; Medio-Simon, M.; Sedgwick, D. M.; Santi, C.; Ruzziconi, R.; Soloshonok, V. A. Chem. Eur. J. 2019, 25, 11797-11819.

  • Mullard, A. Nat. Rev. Drug Discovery 2019, 18, 85 - 89.

  • Baedeker, M.; Ringel, M.; Schulze, U. Nat. Rev. Drug Discovery 2019, 18, 90.

  • Mullard, A. Nat. Rev. Drug Discovery 2020, 19, 79 - 84.

  • Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073-9174.

  • Lee, J.-W.; Oliveira, M. T.; Jang, H. B.; Lee, S.; Chi, D. Y.; Kim, D. W.; Song, C. E. Chem. Soc. Rev. 2016, 45, 4638-4650.

  • Yerien, D. E.; Bonesi, S.; Postigo, A. Org. Biomol. Chem. 2016, 14, 8398-8427.

  • Liang, S.; Hammond, G. B.; Xu, B. Chem. - Eur. J. 2017, 23, 17850-17861.

  • Langlois, B.; Gilbert, L.; Forat, G., Fluorination of aromatic compounds by halogen exchange with fluoride anions (“halex” reaction). In Industrial Chemistry Library, Desmurs, J.-R.; Ratton, S., Eds. Elsevier: 1996; Vol. 8, pp 244-292.

  • Sharma, R. K.; Fry, J. L. J. Org. Chem. 1983, 48, 2112-2114.

  • Melvin, P. R.; Ferguson, D. M.; Schimler, S. D.; Bland, D. C.; Sanford, M. S. Org. Lett. 2019, 21, 1350-1353.

  • Pupo, G.; Ibba, F.; Ascough, D. M. H.; Vicini, A. C.; Ricci, P.; Christensen, K. E.; Pfeifer, L.; Morphy, J. R.; Brown, J. M.; Paton, R. S.; Gouverneur, V. Science 2018, 360, 638-642.

  • Bouvet, S.; Pégot, B.; Marrot, J.; Magnier, E. Tetrahedron Lett. 2014, 55, 826-829.

  • Chen, Z.; Tonouchi, Y.; Matsumoto, K.; Saimura, M.; Atkin, R.; Nagata, T.; Katahira, M.; Hagiwara, R. J. Phys. Chem. Lett. 2018, 9, 6662-6667.

  • Enomoto, T.; Nakamori, Y.; Matsumoto, K.; Hagiwara, R. J. Phys. Chem. C 2011, 115, 4324-4332.

  • Ryan, S. J.; Schimler, S. D.; Bland, D. C.; Sanford, M. S. Org. Lett. 2015, 17, 1866-1869.

  • Tang, P.; Wang, W.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 11482–11484.

  • Goldberg, N. W.; Shen, X.; Li, J.; Ritter, T. Org. Lett. 2016, 18, 6102-6104.

  • Hayashi, H.; Sonoda, H.; Fukumura, K.; Nagata, T. Chem. Commun. 2002, 1618-1619.

  • Alič, B.; Tavčar, G. J. Fluorine Chem. 2016, 192, 141-146.

  • Alič, B.; Tramšek, M.; Kokalj, A.; Tavčar, G. Inorg. Chem. 2017, 56, 10070-10077.

  • Zupanek, Ž.; Tramšek, M.; Kokalj, A.; Tavčar, G. Inorg. Chem. 2018, 57, 13866-13879.

  • Sun, H.; DiMagno, S. G. J. Am. Chem. Soc. 2005, 127, 2050-2051.

  • Szarek, W. A.; Hay, G. W.; Doboszewski, B. J. Chem. Soc., Chem. Commun. 1985, 663-4.

  • Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166-5167.

  • Kvíčala, J.; Mysík, P.; Paleta, O. Synlett 2001, 547-549.

  • Yamaguchi, S.; Akiyama, S.; Tamao, K. Organometallics 1999, 18, 2851-2854.

  • Albanese, D.; Landini, D.; Penso, M. Tetrahedron Lett. 1995, 36, 8865-6.

  • Kvíčala, J. Unpublished results.

  • Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119-6146.

  • Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1-PR43, Web Only Content.

  • Chen, C.; Fu, L.; Chen, P.; Liu, G. Chin. J. Chem. 2017, 35, 1781-1788.

  • Zhu, Y.; Han, J.; Wang, J.; Shibata, N.; Sodeoka, M.; Soloshonok, V. A.; Coelho, J. A. S.; Toste, F. D. Chem. Rev. 2018, 118, 3887-3964.

  • Hann, G. L.; Sampson, P. J. Chem. Soc., Chem. Commun. 1989, 1650-1.

  • Beaumont, A. J.; Kiely, C.; Denise Rooney, A. J. Fluorine Chem. 2001, 108, 47-50.

  • Katcher, M. H.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 17402-17404.

  • Katcher, M. H.; Sha, A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 15902-15905.

  • Zhang, Q.; Stockdale, D. P.; Mixdorf, J. C.; Topczewski, J. J.; Nguyen, H. M. J. Am. Chem. Soc. 2015, 137, 11912-5.

  • Sather, A. C.; Lee, H. G.; De La Rosa, V. Y.; Yang, Y.; Muller, P.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 13433-13438.

  • Hollingworth, C.; Gouverneur, V. Chem. Commun. 2012, 48, 2929-2942.

  • Inoue, M.; Sumii, Y.; Shibata, N. ACS Omega 2020, Ahead of Print.

  • Tressaud, A., Fluorine, a key element for the 21st century. In Fluorine, Tressaud, A., Ed. Elsevier: 2019; Vol. 5, pp 77-150.

  • Fuge, R. Appl. Geochem. 2019, 100, 393-406.

  • Yang, L.; Dong, T.; Revankar, H. M.; Zhang, C.-P. Green Chem. 2017, 19, 3951-3992.

  • Harsanyi, A.; Sandford, G. Green Chem. 2015, 17, 2081-2086.

  • Makosza, M.; Bujok, R. J. Fluorine Chem. 2005, 126, 209-216.

  • Hintermann, L. Beilstein J. Org. Chem. 2007, 3.

  • Mahjoub, A. R.; Zhang, X.; Seppelt, K. Chem. - Eur. J. 1995, 1, 261-5.

  • Jones, S. C.; Davis, V. K.; Bates, C. M.; Momcilovic, N.; Savoie, B. M.; Webb, M. A.; Miller, T. F., III; Grubbs, R. H.; Murphy, J. M. US20170057908A1, 2017.
  • Braun, C.; Braese, S.; Schafer, L. L. Eur. J. Org. Chem. 2017, 2017, 1760-1764.

  • Simko, D. C.; Elekes, P.; Pazmandi, V.; Novak, Z. Org. Lett. 2018, 20, 676-679.

  • Dalessandro, E. V.; Pliego Jr, J. R. Theor. Chem. Acc. 2020, 139, 27pp.


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