Highly chemoselective rhodium-catalyzed methylenation of fluorine-containing ketones

Organic Letters

Volumn 4, Issue 10, 2002, Pages 1671-1674

  Lebel, Hélène ^a   Paquet, Valérie ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORINE; KETONE; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY; GAS CHROMATOGRAPHY; METHYLATION; SYNTHESIS;

ALKENES; CATALYSIS; CHROMATOGRAPHY, GAS; FLUORINE; INDICATORS AND REAGENTS; KETONES; METHYLATION; RHODIUM;

EID: 0037118361     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025730l     Document Type: Article

References (47)

1. (a) Welch, J. T. Tetrahedron 1987, 43, 3123.
2. (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
3. (b) Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II: A Critical Review. ACS Monograph Series 187; American Chemical Society: Washington, DC, 1995.
4. (c) Baasner, B.; Hagemann, H.; Tatlow, J. C. Organo-Fluorine Compounds; Houben-Weyl: Thieme, 1999; Vols. 1-5.
5. (d) Schofield, H. J. Fluorine Chem. 1999, 100, 7-11.
6. (e) Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431-12477.
7. (a) Synthetic Fluorine Chemistry; Olah, G. A., Prakash, G. K. S., Chambers, R. D., Eds.; Wiley; New York, 1992.
8. (b) McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555-6666.
9. (c) Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786.
10. (d) Fei, X. S.; Tian, W. S.; Chen, Q. Y. J. Chem. Soc., Perkin Trans. 1 1998, 1139-1142.
11. (e) Sanin, A. V.; Nenajdenko, V. G.; Smolko, K. I.; Denisenko, D. I.; Balenkova, E. S. Synthesis 1998, 842-846.
12. (f) Singh, R. P.; Shreeve, J. M. Tetrahedron 2000, 56, 7613-7632.
13. (g) Billard, T.; Bruns, S.; Langlois, B. R. Org. Lett. 2000, 2, 2101-2103.
14. (h) Singh, R. P.; Shreeve, J. M. J. Org. Chem. 2000, 65, 3241-3243.
15. (i) Singh, R. P.; Leitch, J. M.; Twamley, B.; Shreeve, J. M. J. Org. Chem. 2001, 66, 1436-1440.
16. (a) Chambers, R. D.; Vaughan, J. F. S. Top. Curr. Chem. 1997, 192, 1-38.
17. (b) Percy, J. M. Top. Curr. Chem. 1997, 193, 131-195.
18. (c) Lin, P.; Jiang, J. L. Tetrahedron 2000, 56, 3635-3671.
19. For selected examples, see: (a) Hanzawa, Y.; Suzuki, M.; Kobayashi, Y.; Taguchi, T. J. Org. Chem. 1991, 56, 1718-1725.
20. (b) De Clercq, P. J.; Zhu, G. D.; Vanlancker, B.; Vanhaver, D.; Declercq, P. J. Bull. Soc. Chim. Belg. 1994, 103, 263-271.
21. (c) Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600.
22. (d) Nemoto, H.; Satoh, A.; Fukumoto, K. Tetrahedron 1995, 51, 10159-10174.
23. (e) Ichikawa, J.; Fujiwara, M.; Okauchi, T.; Minami, T. Synlett 1998, 927-929.
24. (f) Komatsu, Y.; Sakamoto, T.; Kitazume, T. J. Org. Chem. 1999, 64, 8369-8374.
25. (a) Begue, J. P.; Bonnetdelpon, D.; Rock, M. H. Synlett 1995, 6, 659-660.
26. (b) Begue, J. P.; Bonnetdelpon, D.; Rock, M. H. Tetrahedron Lett. 1995, 36, 5003-5006.
27. (c) Begue, J. P.; Bonnetdelpon, D.; Bouvet, D.; Rock, M. H. J. Org. Chem. 1996, 61, 9111-9114.
28. (d) Begue, J. P.; Bonnetdelpon, D.; Rock, M. H. J. Chem. Soc., Perkin Trans. 1996, 21, 1409-1413.
29. For selected examples, see: (a) Jiang, B. A.; Xu, Y. Y. Tetrahedron Lett. 1992, 33, 511-514.
30. (b) Iseki, K.; Kuroki, Y.; Nagai, T.; Kobayashi, Y. J. Fluorine Chem. 1994, 69, 5-6.
31. (c) Nader, B. S.; Cordova, J. A.; Reese, K. E.; Powell, C. L. J. Org. Chem. 1994, 59, 2898-2901.
32. (d) Peng, S.; Qing, F. L.; Guo, Y. L. Synlett 1998, 859-860.
33. (a) Nader, B. S.; Cordova, J. A.; Reese, K. E.; Powell, C. L. J. Org. Chem. 1994, 59, 2898-2901.
34. (b) Begue, J. P.; Bonnetdelpon, D.; Kornilov, A. Org. Synth. 1998, 75, 153-160.
35. (c) Faure, S.; Piva, O. Synlett 1998, 12, 1414-1416.
36. (d) Yoshimatsu, M.; Sugimoto, T.; Okada, N.; Kinoshita, S. J. Org. Chem. 1999, 64, 5162-5165.
37. (e) Shen, Y. C.; Ni, J. H.; Li, P.; Sun, J. J. Chem. Soc., Perkin Trans, 1 1999, 509-512.
38. Lebel, H.; Paquet, V.; Proulx, C. Angew. Chem., Int. Ed. 2001, 40, 2887-2890.
39. (a) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195-2202.
40. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
41. (c) Furstner, A. Angew. Chem, Int. Ed. 2000, 39, 3013-3043.
42. (a) Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393-395.
43. (b) Singh, R. P.; Cao, G.; Kirchmeier, R.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2873-2876.
44. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
45. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
46. (c) Linderman, R. J.; Graves, D. M. J. Org. Chem. 1989, 54, 661-668.
47. Although there are some procedures for the direct preparation of trifluoromethylketones from carboxylic esters, those require the use of rigously anhydrous TBAF; see: Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G. K. S.; Olah, G. A. Angew. Chem., Int. Ed. 1998, 37, 820-821. We found it more practical to use the two-step procedure described above.