Synthesis and elaboration of all-cis-1,2,4,5-tetrafluoro-3- phenylcyclohexane: A polar cyclohexane motif

Chemistry - A European Journal

Volumn 20, Issue 21, 2014, Pages 6259-6263

  Durie, Alastair J ^a   Fujiwara, Tomoya ^a,b   Cormanich, Rodrigo ^a   Bühl, Michael ^a   Slawin, Alexandra M Z ^a   O'Hagan, David ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

aromatic transformations; cyclohexane; fluorinations; organofluorine compounds; polar organic motifs

Indexed keywords

FLUORINATION; HYDROGEN BONDS;

ARYL GROUP; CYCLOHEXANE RING; CYCLOHEXYL RINGS; MOLECULAR BUILDING BLOCKS; NMR COUPLING; ORGANOFLUORINE COMPOUNDS; POLAR ORGANIC MOTIFS; STEREOCONTROLLED SYNTHESIS;

CYCLOHEXANE;

EID: 84900826064     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201400354     Document Type: Article

References (36)

1. D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319
2. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886.
3. P. Tang, W. Wang, T. Ritter, J. Am. Chem. Soc. 2011, 133, 11482-11484
4. D. A. Watson, M. Su, G. Teverovskiy, Y. Zhang, J. García-Fortanet, T. Kinzel, S. L. Buchwald, Science 2009, 325, 1661-1664.
5. F. Sladojevich, S. I. Arlow, P. Tang, T. Ritter, J. Am. Chem. Soc. 2013, 135, 2470-2473
6. D. O'Hagan, J. Org. Chem. 2012, 77, 3689-3699.
7. G. Landelle, A. Panossian, S. Pazenok, J.-P. Vors, F. R. Leroux, Beilstein J. Org. Chem. 2013, 9, 2476-2536
8. D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224-228
9. W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369.
10. F. R. Leroux, B. Manteau, J.-P. Vors, S. Pazenok, Beilstein J. Org. Chem. 2008, 4, 13
11. V. N. Boiko, Beilstein J. Org. Chem. 2010, 6, 880-921.
12. P. Kirsch, in Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications, 2nd Ed., Wiley-VCH, Weinheim, Germany, 2013
13. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330
14. P. Jeschke, ChemBioChem 2004, 5, 570-589.
15. S. Hruschka, S. Yoshida, K. L. Kirk, G. Haufe, J. Fluorine Chem. 2008, 129, 875-880.
16. S. A. Künzi, B. Morandi, E. M. Carreira, Org. Lett. 2012, 14, 1900-1901
17. B. Morandi, J. Cheang, E. M. Carreira, Org. Lett. 2011, 13, 3080-3081
18. F. Wang, T. Luo, J. B. Hu, Y. Wang, H. S. Krishnan, P. V. Jog, S. K. Ganesh, G. K. S. Prakash, G. A. Olah, Angew. Chem. 2011, 123, 7291-7295
19. Angew. Chem. Int. Ed. 2011, 50, 7153-7157.
20. A. J. Durie, A. M. Z. Slawin, T. Lebl, P. Kirsch, D. O'Hagan, Chem. Commun. 2012, 48, 9643-9645.
21. P. A. Baguley, L. V. Jackson, J. C. Walton, J. Chem. Soc. Perkin Trans. 1 2002, 304-309.
22. W. J. Middleton, J. Org. Chem. 1975, 40, 574-578.
23. G. S. Lal, G. P. Pez, R. J. Pesaresi, F. M. Prozonic, H. Cheng, J. Org. Chem. 1999, 64, 7048-7054
24. G. S. Lal, G. P. Pez, R. J. Pesaresi, F. M. Prozonic, Chem. Commun. 1999, 215-216.
25. G. Haufe, J. Prakt. Chem./Chem.-Ztg. 1996, 338, 99-113.
26. J. A. K. Howard, V. J. Hoy, D. O'Hagan, G. T. Smith, Tetrahedron 1996, 52, 12613-12622
27. J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89-98
28. S. J. Borwick, J. A. K. Howard, C. W. Lehmann, D. O'Hagan, Acta Crystallogr. C 1997, C53, 124-126.
29. G. T. Giuffredi, V. Gouverneur, B. Bernet, Angew. Chem. Int. Ed. 2013, 52, 10524-10528
30. S. Jaime-Figueroa, L. J. Kurz, Y. Liu, R. Cruz, Spectrochim. Acta Part A 2000, 56, 1167-1178
31. A. Mele, B. Vergani, F. Viani, S. V. Meille, A. Farina, P. Bravo, Eur. J. Org. Chem. 1999, 187-196
32. A. Mele, G. Salani, F. Viani, P. Bravo, Mag. Res. Chem. 1997, 35, 168-174
33. G. W. Gribble, W. J. Kelly, Tetrahedron Lett. 1985, 26, 3779-3782.
34. J. V. Crivello, J. Org. Chem. 1981, 46, 3056-3060
35. J. M. Mellor, S. Mittoo, R. Parkes, R. W. Millar, Tetrahedron 2000, 56, 8019-8024.
36. N. Azizi, A. Khajeh-Amiri, H. Ghafuri, M. Bolourtchian, M. R. Saidi, Synlett 2009, 2245-2248.