Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 8131-8141

  Kelly, Christopher B ^a   Mercadante, Michael A ^a   Hamlin, Trevor A ^a   Fletcher, Madison H ^a   Leadbeater, Nicholas E ^a,b  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b UNIVERSITY OF CONNECTICUT HEALTH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BASIC CONDITIONS; TETRAFLUOROBORATES; TRIFLUOROMETHYL; TRIFLUOROMETHYLKETONE;

HYDRATES; KETONES;

OXIDATION;

4 ACETYLAMINO 2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXOAMMONIUM TETRAFLUOROBORATE; ALPHA TRIFLUOROMETHYL ALCOHOL DERIVATIVE; AMMONIA; KETONE DERIVATIVE; METHANOL; SODIUM CHLORIDE; TRIFLUOROMETHYL KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; OXIDATION; STEREOCHEMISTRY;

ALCOHOLS; BORATES; CYCLIC N-OXIDES; METHANOL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PIPERIDINES; QUATERNARY AMMONIUM COMPOUNDS; SALTS;

EID: 84868142094     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301477s     Document Type: Article

References (61)

1. (a) Hiyama, T. Organofluorine Compounds. Chemistry and Applications; Springer: New York, 2000.
2. (b) O'Hagan, D.; Harper, D. B. J. Fluorine Chem. 1999, 100, 127.
3. (c) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
4. (d) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
5. (e) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013.
6. (f) Smart, B. E. J. Fluorine Chem. 2001, 109, 3.
7. (a) Ismail, F. M. D. J. Fluorine Chem. 2002, 118, 27.
8. (b) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
9. Shao, Y.-M.; Yang, W.-B.; Kuo, T.-H.; Tsai, K.-C.; Lin, C.-H.; Yang, A.-S.; Liang, P.-H.; Wong, C.-H. Bioorg. Med. Chem. 2008, 16, 4652.
10. (b) Garrett, G. S.; McPhail, S. J.; Tornheim, K.; Correa, P. E.; McIver, J. M. Bioorg. Med. Chem. Lett. 1999, 9, 301.
11. (c) Veale, C. A.; Damewood, J. R., Jr.; Steelman, G. B.; Bryant, C.; Gomes, B.; Williams, J. J. Med. Chem. 1996, 38, 86.
12. (a) Abid, M.; Török, B. Adv. Synth. Catal. 2005, 347, 1797.
13. (b) Zanatta, N.; Schneider, J. M. F. M.; Schneider, P. H.; Wouters, A. D.; Bonacorso, H. G.; Martins, M. A. P.; Wessjohann, L. A. J. Org. Chem. 2006, 71, 6996.
14. (c) Kiss, L. E.; Ferreira, H. S.; Learmonth, D. A. Org. Lett. 2008, 10, 1835.
15. (a) Baskakis, C.; Magrioti, V.; Cotton, N.; Stephens, D.; Constantinou-Kokotou, V.; Dennis, E. A.; Kokotos, G. J. Med. Chem. 2008, 51, 8027.
16. (b) Rodeschini, V.; Van de Weghe, P.; Salomon, E.; Tarnus, C.; Eustache, J. J. Org. Chem. 2005, 70, 2409.
17. (a) Grellepois, F.; Chorki, F.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J.-P. J. Org. Chem. 2002, 67, 1253.
18. (b) Riber, D.; Venkataramana, M.; Sanyal, S.; Duvold, T. J. Med. Chem. 2006, 49, 1503.
19. (a) Pierce, M. E.; Parsons, R. L., Jr.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D.; Luo, C.; Morgan, S. J.; Davis, W. P.; Confalone, P. N. J. Org. Chem. 1998, 63, 8536.
20. (b) Nicolaou, K. C.; Krasovskiy, A.; Majumder, U.; Trépanier, V. É.; Chen, D. Y.-K. J. Am. Chem. Soc. 2009, 131, 3690.
21. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813.
22. Bégué, J.-P.; Bonnet-Delpon, D. Tetrahedron 1991, 47, 3207.
23. Linderman, R. J.; Graves, D. M. Tetrahedron Lett. 1987, 28, 4259.
24. Linderman, R. J.; Graves, D. M. J. Org. Chem. 1989, 54, 661.
25. Kesavan, V.; Bonnet-Delpon, D.; Bégué, J.-P.; Srikanth, A.; Chandrasekaran, S. Tetrahedron Lett. 2000, 41, 3327.
26. Plumb, J. B.; Harper, D. J. Chem. Eng. News 1990, 68, 2-3,45.
27. Baxendale, I. R.; Ley, S. V.; Lumeras, W.; Nesi, M. Comb. Chem. High Throughput Screening 2002, 5, 197.
28. For reviews see: (a) deNooy, A. E. J.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153.
29. (b) Adam, W.; Saha-Moller, C. R.; Ganeshpure, P. A. Chem. Rev. 2001, 101, 3499.
30. (c) Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774.
31. (d) Ciriminna, R.; Pagliaro, M. Org. Process Res. Dev. 2010, 14, 245.
32. Abell, A. D.; Pearson, D.; Alexander, N. Chem. Eur. J. 2008, 14, 7358.
33. Litvinas, N. D.; Brodsky, B. H.; Du Bois, J. Angew. Chem., Int. Ed. 2009, 48, 4513.
34. For the use of this reagent see: (a) Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367.
35. (b) Bobbitt, J. M.; Merbouh, N. Org. Synth. 2005, 82, 80.
36. (c) Bailey, W. F.; Bobbitt, J. M.; Wiberg, K. B. J. Org. Chem. 2007, 72, 4504.
37. (d) Bobbitt, J. M.; Bruckner, C.; Merbouh, N. Org. React. 2010, 74, 103.
38. (e) Pradhan, P. P.; Bobbitt, J. M.; Bailey, W. F. J. Org. Chem. 2009, 74, 9524.
39. (f) Merbouh, N.; Bobbitt, J. M.; Bruckner, C. J. Org. Chem. 2004, 69, 5116.
40. (g) Qui, J.; Pradhan, P. P.; Blanck, N. B.; Bobbitt, J. M.; Bailey, W. F. Org. Lett. 2012, 14, 350.
41. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984.
42. Bartelson, A. L. Novel Reactions of Oxoammonium Salts in the Presence of Base, Graduate Thesis, University of Connecticut, Storrs, CT, 2011.
43. Mullet, G. M.; Nodding, C. R. Science 1962, 138, 1346.
44. Furuya, T.; Kaiser, H. M.; Ritter, T. Angew. Chem., Int. Ed. 2008, 47, 5993.
45. Chen, P.; Xu, Q.; Zhou, H.; Geng, X. Tetrahedron 2009, 65, 2232.
46. Kelly, C. B.; Colthart, A. M.; Constant, B. D.; Corning, S. R.; Dubois, L. N. E.; Genovese, J. T.; Radziewicz, J. L.; Sletten, E. M.; Whitaker, K. R.; Tilley, L. J. Org. Lett. 2011, 13, 1646.
47. Chen, P.; Xu, Q.; Zhou, H.; Geng, X. Tetrahedron 2009, 65, 2232.
48. Burns, B. H. et al. Triazolyl Aminopyrimidine Compounds; Patent WO 2008144223, November 27, 2008.
49. Watanabe, S.; Fujita, T.; Sakamoto, M.; Mino., Y.; Kitazume, T. J. Fluorine Chem. 1995, 73, 21.
50. Ahn, K. H.; Kim, D. S. J. Org. Chem. 2008, 73, 6831.
51. Nobuyoshi, A. et al. Kynurenine Production Inhibitor; Patent US 2011237584, September 29, 2011.
52. Gerus, I. I.; Gorbunova, M. G.; Kukhar, V. P. J. Fluorine Chem. 1993, 65, 25.
53. Belot, A.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem., Int. Ed. 2009, 48, 8923.
54. Lovely, C. J.; Lima, H. M.; Sivappa, R.; Yousufuddin, M. Org. Lett. 2012, 14, 2274.
55. Nagano, T.; Kawabata, E.; Kikuchi, K.; Urano, Y.; Kojima, H.; Odani, A. J. Am. Chem. Soc. 2005, 127, 818.
56. Tanner, D.; Wennerstrom, O. Acta Chem. Scand., Ser. B 1983, 37, 693.
57. Sustmann, R.; Endtner, R.; Rentschler, E.; Blaser, D.; Boese, R. Eur. J. Org. Chem. 2000, 19, 3347.
58. Roche, A. J.; Loyle, A. D.; Pinto, J. P. J. Fluorine Chem. 2004, 125, 1473.
59. Tyrra, W.; Kremlev, M. M.; Mushta, A. I.; Naumann, D.; Fischer, H. T. M.; Yagupolskii, Y. L. J. Fluorine Chem. 2007, 128, 1385.
60. Srogl, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2000, 122, 11260.
61. Ohno, A.; Nakai, J.; Nakamura, K. Bull. Chem. Soc. Jpn. 1981, 54, 3482.