Display options
Share it on

Synlett. 2016 Dec;27(20):2747-2755. doi: 10.1055/s-0036-1588637.

Metal-catalyzed Decarboxylative Fluoroalkylation Reactions.

Synlett : accounts and rapid communications in synthetic organic chemistry

Brett R Ambler, Ming-Hsiu Yang, Ryan A Altman

Affiliations

  1. Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, United States.

PMID: 28260839 PMCID: PMC5330304 DOI: 10.1055/s-0036-1588637

Abstract

Metal-catalyzed decarboxylative fluoroalkylation reactions enable the conversion of simple O-based substrates into biologically relevant fluorinated analogs. Herein, we present decarboxylative methods that facilitate the synthesis of trifluoromethyl- and difluoroketone-containing products. We highlight key mechanistic aspects that are critical for efficient catalysis, and that inspired our thinking while developing the reactions.

Keywords: Catalysis; Copper; Decarboxylation; Difluoroketone; Fluorine; Palladium; Trifluoromethylation

References

  1. Chem Rev. 1997 May 8;97(3):757-786 - PubMed
  2. Chemistry. 2002 Aug 16;8(16):3620-8 - PubMed
  3. J Org Chem. 2005 Jul 8;70(14):5760-3 - PubMed
  4. Angew Chem Int Ed Engl. 2007;46(9):1373-5 - PubMed
  5. J Am Chem Soc. 2007 Jun 27;129(25):7718-9 - PubMed
  6. J Am Chem Soc. 2007 Oct 3;129(39):11876-7 - PubMed
  7. Chem Commun (Camb). 2007 Sep 14;(34):3583-5 - PubMed
  8. J Am Chem Soc. 2010 Jul 14;132(27):9280-2 - PubMed
  9. Chem Rev. 2011 Mar 9;111(3):1846-913 - PubMed
  10. Chem Rev. 2011 Aug 10;111(8):4475-521 - PubMed
  11. Org Lett. 2011 Jul 15;13(14):3596-9 - PubMed
  12. Chem Soc Rev. 2011 Oct;40(10):5030-48 - PubMed
  13. J Am Chem Soc. 2011 Sep 14;133(36):14180-3 - PubMed
  14. J Am Chem Soc. 2011 Dec 28;133(51):20901-13 - PubMed
  15. Chem Commun (Camb). 2012 Feb 11;48(13):1919-21 - PubMed
  16. Org Lett. 2012 Aug 3;14(15):3966-9 - PubMed
  17. Chemistry. 2012 Oct 15;18(42):13255-8 - PubMed
  18. J Am Chem Soc. 2012 Nov 21;134(46):19050-60 - PubMed
  19. J Med Chem. 2013 Mar 28;56(6):2456-65 - PubMed
  20. J Org Chem. 2013 Jul 19;78(14):7330-6 - PubMed
  21. Angew Chem Int Ed Engl. 2013 Aug 5;52(32):8214-64 - PubMed
  22. Chem Commun (Camb). 2013 Sep 14;49(71):7809-11 - PubMed
  23. J Org Chem. 2013 Nov 15;78(22):11126-46 - PubMed
  24. Org Lett. 2013 Nov 1;15(21):5578-81 - PubMed
  25. Beilstein J Org Chem. 2013 Dec 12;9:2862-5 - PubMed
  26. Curr Top Med Chem. 2014;14(7):966-78 - PubMed
  27. Angew Chem Int Ed Engl. 2014 Mar 10;53(11):2826-51 - PubMed
  28. J Am Chem Soc. 2014 Mar 19;136(11):4149-52 - PubMed
  29. Org Biomol Chem. 2014 May 14;12(18):2903-6 - PubMed
  30. Chem Rev. 2015 Jan 28;115(2):683-730 - PubMed
  31. Org Biomol Chem. 2014 Aug 14;12(30):5594-6 - PubMed
  32. Synthesis (Stuttg). 2014 Jul 15;46(14):1938-1946 - PubMed
  33. Chem Rev. 2015 Feb 25;115(4):1847-935 - PubMed
  34. Org Lett. 2015 May 15;17(10):2506-9 - PubMed
  35. J Org Chem. 2015 Aug 21;80(16):8449-57 - PubMed
  36. Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10396-400 - PubMed
  37. Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10401-5 - PubMed
  38. Angew Chem Int Ed Engl. 1998 Feb 16;37(3):323-325 - PubMed

Publication Types

Grant support