1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): A versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via JuliaKocienski olefination

Tetrahedron

Volumn 66, Issue 27-28, 2010, Pages 5089-5100

  Zhu, Lingui ^a   Ni, Chuanfa ^a   Zhao, Yanchuan ^a   Ru, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Fluoromethyl sulfone Monofluroalkene JuliaKocienski olefination Fluoroolefination

Indexed keywords

1 TERT BUTYL 1H TETRAZOL 5 YLFLUOROMETHYLSULFONE; ALDEHYDE; ALKENE; BASE; FLUORINE DERIVATIVE; KETONE; SOLVENT; SULFONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; JULIA KOCIENSKI OLEFINATION; OLEFINATION; OXIDATION; PRIORITY JOURNAL; REACTION OPTIMIZATION; SCREENING; SOLVENT EFFECT; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 77954349459     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.113     Document Type: Article

References (66)

1. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, UK, 2006
2. (b) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim.
3. (c) Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, 2004
4. (d) Begue, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley: Hoboken, USA, 2008
5. (e) Organofluorine Compounds. Chemistry and Applications; Hiyama, T., Ed.; Springer: New York, NY, 2000
6. (f) Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum: New York, NY, 1994.
7. Ameduri, B.; Boutevin, B. J. Fluorine Chem. 2000, 104, 53-62.
8. McCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B.J.; Synder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991,113, 7439-7440
9. (b) Welch, J. T. Slective Fluorination in Organic and Bioorganic Chemistry; American Chemical Society: Washington, D.C, 1991
10. (c) Weintraub, P. M.; Holland, A. K.; Gates, C. A.; Moore, W. R.; Resvick, R. J.; Beye, P.; Peet, N. P. Bioorg. Med. Chem. 2003, 11, 427-431.
11. Fluorine-Containing Synthons; Soloshonok, V. A., Ed.; American Chemical Society: Washington, DC, 2005.
12. Steenis, J. H.; Gen, A. J. Chem. Soc., Perkin Trans. 1 2002, 2117-2133.
13. Lee, S. H.; Schwartz, J. J. Am. Chem. Soc. 1986, 108, 2445-2447.
14. (a) Tius, M. A.; Kawakami, J. K. Synlett 1993, 207-208
15. (b) Tius, M. A.; Kawa-kami, J. K. Tetrahedron 1995, 51, 3997-4010.
16. (a) Manfre, F.; Kern, J. M.; Biellmann, J.-F. J. Org. Chem. 1992, 57,2060-2065
17. (b) Burton, D. J.; Cox, D. G. J. Am. Chem. Soc. 1983, 105, 650-651
18. (c) Cox, D. G.; Gurusamy, N.; Burton, D.J. J. Am. Chem. Soc. 1985, 107, 2811-2812
19. (d) Wheaton, G. A.; Burton, D.J. J. Org. Chem. 1983, 48, 917-927
20. (e) van Steenis, J. H.; van der Gen, A. Eur. J. Org. Chem. 2001, 897-910.
21. (a) McCarthy, J. R.; Matthews, D. P.; Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T. Tetrahedron Lett. 1990, 31, 5449-5452
22. (b) Khrimian, A. P.; DeMilo, A. B.; Waters, R. M.; Liquido, N.J.; Nicholson, J. M. J. Org. Chem. 1994, 59, 8034-8039.
23. Zhang, W.; Huang, W.; Hu, J. Angew. Chem., Int. Ed. 2009, 48, 9858-9861.
24. (a) Chevrie, D.; Lequeux, T.; Demoute, J. P.; Pazenok, S. Tetrahedron Lett. 2003, 44, 8127-8130
25. (b) Pfund, E.; Lebargy, C.; Rouden, J.; Lequeux, T.J. Org. Chem. 2007, 72, 7871-7877
26. (c) Calata, C.; Catel, J.-M.; Pfund, E.; Lequeux, T. Tetrahedron 2009, 65, 3967-3973
27. (d) Calata, C.; Pfund, E.; Lequeux, T. J. Org. Chem. 2009, 74, 9399-9405.
28. (a) Ghosh, A. K.; Zajc, B. Org. Lett. 2006, 8, 1553-1556
29. (b) Zajc, B.; Kake, S. Org. Lett. 2006, 8, 4457-4460
30. (c) del Solar, M.; Ghosh, A. K.; Zajc, B. J. Org. Chem. 2008, 73, 8206-8211
31. (d) He, M.; Ghosh, A. K.; Zajc, B. Synlett 2008, 999-1004
32. (e) Ghosh, A. K.; Banerjee, S.; Sinha, S.; Kang, S. B.; Zajc, B. J. Org. Chem. 2009, 74, 3689-3697
33. (f) Ghosh, A. K.; Zajc, B. J. Org. Chem. 2009, 74, 8531-8540.
34. Alonso, D. A.; Fuensanta, M.; Gomez-Bengoa, E.; Najera, C. Adv. Synth. Catal. 2008, 350, 1823-1829.
35. (a) Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Tetrahedron Lett. 1991, 32, 1175-1178
36. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26-28
37. (c) Kocienski, P. J.; Bell, A.; Blakemore, P. R. Synlett 2000, 365-366
38. (d) Blakemore, P. R. J. Chem. Soc., PerkinTrans. 1 2002, 2563-2585
39. (e) Aissa, C. Eur. J. Org. Chem. 2009, 1831-1844
40. (f) Takeda, T. Modern Carbonyl Olefination; Wiley-VCH: Weinheim, 2004.
41. Zhang, W.; Zhu, L.; Hu, J. Tetrahedron 2007, 63, 10569-10575.
42. Both PTSO2CH2F (2b) and TBTSO2CH2F (2c) are previously unknown, and BTSO2CH2F (2a) was recently reported as an undesired product [see Ref. 11c]. We found that fluoromethyl heteroaryl sulfone compounds were difficult to be prepared by electrophilic fluorination of corresponding methyl sulfones (see below).
43. (a) Li, Y.; Hu, J. Angew. Chem., Int. Ed. 2005, 44, 5882-5886
44. (b) Li, Y.; Ni, C.; Liu, J.; Zhang, L.; Zheng, J.; Zhu, L.; Hu, J. Org. Lett. 2006, 8, 1693-1696
45. (c) Ni, C.; Li, Y.; Hu, J. J. Org. Chem. 2006, 71, 6829-6833
46. (d) Ni, C.; Liu, J.; Zhang, L.; Hu, J. Angew. Chem., Int. Ed. 2007, 46, 786-789
47. (e) Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921-930
48. (f) Liu, J.; Li, Y.; Hu, J. J. Org. Chem. 2007, 72, 3119-3121
49. (g) Ni, C.; Zhang, L.; Hu, J. J. Org. Chem. 2008, 73, 5699-5713
50. (h) Ni, C.; Zhang, L.; Hu, J. J. Org. Chem. 2009, 74, 3767-3771
51. (i) Hu, J. J. Fluorine Chem. 2009, 130, 1130-1139.
52. Please see experimental section.
53. Su, W. Tetrahedron Lett. 1994, 35, 4955-4958.
54. Surprenant, S.; Chan, W. Y.; Berthelette, C. Org. Lett. 2003, 5, 4851-4854.
55. Kataoka, K.; Tsuboi, S. Synthesis 1999, 452-456.
56. Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772-10773.
57. Prakash, G. S. K.; Chacko, S.; Vaghoo, H.; Shao, N.; Gurung, L.; Mathew, T.; Olah, G. A. Org. Lett. 2009, 11, 1127-1130.
58. (a) Quast, H.; Bieber, L. Chem. Ber. 1981, 114, 3253-3272
59. (b) Aissa, C. J. Org. Chem. 2006, 71, 360-363.
60. Wang, R.; Dolman, S. J. J. Org. Chem. 2007, 72, 3969-3971.
61. Adam, W.; Bargon, R. M.; Bosio, S. G.; Schenk, W. A.; Stalke, D. J. Org. Chem. 2002, 67, 7037-7041.
62. Pearson, W. H.; Fang, W.-K. J. Org. Chem. 2000, 65, 7158-7174.
63. Oku, A.; Harada, T.; Hattori, K.; Nozaki, Y.; Yamaura, Y. J. Org. Chem. 1988, 53, 3089-3098.
64. Uno, H.; Sakamoto, K.; Semba, F.; Suzuki, H. Bull. Chem. Soc. Jpn. 1992, 65, 210-217.
65. (a) Asakura, N.; Usuki, Y.; Iio, H. J. Fluorine Chem. 2003, 124, 81-88
66. (b) McCarthy, J. R.; Huber, E. W.; Le, T.-B.; Laskovics, M. F.; Matthews, D. P. Tetrahedron 1996, 52, 45-58.