Direct Oxidation of Organoboranes with Oxygen in Perfluoroalkanes

Synlett

Volumn 1996, Issue 10, 1996, Pages 1004-1006

  Klement, Ingo ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002591954     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5636     Document Type: Article

References (28)

1. For recent applications of perfluorinated solvents: (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72. (b) Zhu, D.-W. Synthesis 1993, 953. (c) Pereira, S. M.; Savage, G. P.; Simpson, G. W. Synth. Commun. 1995, 25, 1023. (d) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (e) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (f) Gladysz, J. A. Science 1994, 266, 55.
2. For recent applications of perfluorinated solvents: (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72. (b) Zhu, D.-W. Synthesis 1993, 953. (c) Pereira, S. M.; Savage, G. P.; Simpson, G. W. Synth. Commun. 1995, 25, 1023. (d) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (e) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (f) Gladysz, J. A. Science 1994, 266, 55.
3. For recent applications of perfluorinated solvents: (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72. (b) Zhu, D.-W. Synthesis 1993, 953. (c) Pereira, S. M.; Savage, G. P.; Simpson, G. W. Synth. Commun. 1995, 25, 1023. (d) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (e) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (f) Gladysz, J. A. Science 1994, 266, 55.
4. For recent applications of perfluorinated solvents: (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72. (b) Zhu, D.-W. Synthesis 1993, 953. (c) Pereira, S. M.; Savage, G. P.; Simpson, G. W. Synth. Commun. 1995, 25, 1023. (d) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (e) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (f) Gladysz, J. A. Science 1994, 266, 55.
5. For recent applications of perfluorinated solvents: (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72. (b) Zhu, D.-W. Synthesis 1993, 953. (c) Pereira, S. M.; Savage, G. P.; Simpson, G. W. Synth. Commun. 1995, 25, 1023. (d) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (e) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (f) Gladysz, J. A. Science 1994, 266, 55.
6. For recent applications of perfluorinated solvents: (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72. (b) Zhu, D.-W. Synthesis 1993, 953. (c) Pereira, S. M.; Savage, G. P.; Simpson, G. W. Synth. Commun. 1995, 25, 1023. (d) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (e) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (f) Gladysz, J. A. Science 1994, 266, 55.
7. Riess, J. G.; Le Blanc, M. Pure Appl. Chem. 1982, 54, 2383.
8. Klement, I.; Knochel, P. Synlett 1995, 1113.
9. (a) Brown, H. C.; Dodson, V. H. J. Am. Chem. Soc. 1957, 79, 2302.
10. (b) Abraham, M. H.; Davies, A. G. J. Chem. Soc. 1959, 429.
11. (c) Brown, H. C.; Negishi, E. J. Am. Chem. Soc. 1971, 93, 6682.
12. (d) Brown, H. C.; Midland, M. M.; Kabalka, G. W. J. Am. Chem. Soc. 1971, 93, 1024.
13. (e) Tanahashi, Y.; Lhomme, J.; Ourisson, G. Tetrahedron 1972, 28, 2655.
14. (f) Brown, H. C.; Midland, M. M.; Kabalka, G. W. Tetrahedron 1986, 42, 5523.
15. (g) Brown, H. C.; Midland, M. M. Tetrahedron 1987, 43, 4059.
16. Köster, R. in Houben-Weyl; Methoden der organischen Chemie. Organobor-Verbindungen III, Band 13, Teil 3c; Thieme Verlag, 1984, p. 329-331.
17. Langer, F.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. Synlett 1994, 410.
18. Kropf, H.; Müller, E.; Weickmann A. in Houben-Weyl Oxidation (Teil I) Methoden der Organischen Chemie , Thieme, 1981, p. 69-168.
19. Chung, T. C.; Janvikul, W.; Lu, L. S. J. Am. Chem. Soc. 1996, 118, 705.
20. (a) Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 6125.
21. (b) Barton, D. H. R.; Jang, D.O.; Jaszberenyi, J. C. Tetrahedron Lett. 1990, 31, 4681.
22. 3B): Köster, R.; Bellut, H.; Fenzl, W. Liebigs Ann. 1974, 54.
23. (a) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691.
24. (b) Rozema, M. J.; AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
25. Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
26. 1 with the axial methyl group a as well as the absence of NOE-cross peaks of the ethyl group e with the axial methyl group a support the stereochemistry of the major isomer 7. See also: (a) Birtwistle, D. H.; Brown, J. M.; Foxton, M. W. Tetrahedron Lett. 1986, 27, 4367. (b) Evans, D. A.; Bartroli, J.; Godel, T. Tetrahedron Lett. 1982, 23, 4577.
27. 1 with the axial methyl group a as well as the absence of NOE-cross peaks of the ethyl group e with the axial methyl group a support the stereochemistry of the major isomer 7. See also: (a) Birtwistle, D. H.; Brown, J. M.; Foxton, M. W. Tetrahedron Lett. 1986, 27, 4367. (b) Evans, D. A.; Bartroli, J.; Godel, T. Tetrahedron Lett. 1982, 23, 4577.
28. 4) and the residue obtained after evaporation of the solvents was purified by flash-chromatography (hexane:ether 9:1) affording the alcohol 2e as a colourless oil (0.79 g, 2.9 mmol, 88 % yield).