Expanding organoboron chemistry: Epoxidation of potassium organotrifluoroborates

Journal of the American Chemical Society

Volumn 125, Issue 37, 2003, Pages 11148-11149

  Molander, Gary A ^a   Ribagorda, María ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE DERIVATIVE; ORGANOBORON DERIVATIVE; POTASSIUM DERIVATIVE;

ARTICLE; COVALENT BOND; EPOXIDATION; MOLECULAR STABILITY; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0042193015     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0351140     Document Type: Article

References (60)

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42. Molander, G. A.; Yun, C.-S.; Ribagorda, M.; Biolatto, B. J. Org. Chem. 2003, 68, 5534-5539. See Supporting Information for preparation of 1, 3d, and 5 and NMR spectra.
43. (a) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 231-285. (c) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.: Springer: Berlin. 1999; pp 649-677. (d) Katsuki In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 287-325.
44. (a) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 231-285. (c) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.: Springer: Berlin. 1999; pp 649-677. (d) Katsuki In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 287-325.
45. (a) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 231-285. (c) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.: Springer: Berlin. 1999; pp 649-677. (d) Katsuki In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 287-325.
46. (a) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 231-285. (c) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.: Springer: Berlin. 1999; pp 649-677. (d) Katsuki In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.: Wiley-Intersience: New York, 2000; pp 287-325.
47. (a) Erden, I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. IA. pp 97-171. (b) Gorzynski Smiyh, J. Synthesis 2002, 629-656.
48. (a) Erden, I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. IA. pp 97-171. (b) Gorzynski Smiyh, J. Synthesis 2002, 629-656.
49. 3 afforded decanal, probably as a consequence of the aqueous basic hydrolysis of the B-F bond in the trifluoroborates (see ref 9a) to a boronic acid or borate that under the peracid conditions affords the enol leading to the aldehyde. Other oxidizing agents such as Davis's oxaziridine or amine N-oxides leave the starting alkenyltrifluoroborate intact.
50. (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (b) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853. (c) Adam, W.; Chan, Y.-Y.; Cremer, D.; Gauss, J.; Scheutzow, D.; Schindler, M. J. Org. Chem. 1987, 52, 2800-2803.
51. (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (b) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853. (c) Adam, W.; Chan, Y.-Y.; Cremer, D.; Gauss, J.; Scheutzow, D.; Schindler, M. J. Org. Chem. 1987, 52, 2800-2803.
52. (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (b) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853. (c) Adam, W.; Chan, Y.-Y.; Cremer, D.; Gauss, J.; Scheutzow, D.; Schindler, M. J. Org. Chem. 1987, 52, 2800-2803.
53. Oxidative B-C bond cleavage with Oxone/acetone is precedented: Webb, K. S.; Levy, D. Tetrahedron Lett. 1995, 35, 5117-5120. We have confirmed that both 1-alkenylboronic acids and the pinacolboronates provide aldehydes quantitatively upon reaction with m-CPBA. Dioxirane oxidation of 1-alkenylboronic acids also provides aldehydes quantitatively, but the corresponding pinacolboronates affords an as yet unidentified oxidation product (not an epoxide) that rapidly decomposes.
54. Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
55. Matteson, D. S. Tetrahedron 1989, 45, 1859-1885.
56. Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4545-4568 and references therein.
57. For examples where an epoxide resides in the electrophilic partner in the Suzuki-Miyaura reaction, see: (a) Falk, J. R.; Kumar, P. S.; Reddy, Y. K.; Zou, G.; Capdevila, J. H. Tetrahedron Lett. 2001, 42, 7211-7212. (b) Falk, J. R.; Kumar, P. S.; Reddy, Y. K.; Zou, G.; Capdevila, J. H. Tetrahedron Lett. 2001, 42, 7213-7215.
58. For examples where an epoxide resides in the electrophilic partner in the Suzuki-Miyaura reaction, see: (a) Falk, J. R.; Kumar, P. S.; Reddy, Y. K.; Zou, G.; Capdevila, J. H. Tetrahedron Lett. 2001, 42, 7211-7212. (b) Falk, J. R.; Kumar, P. S.; Reddy, Y. K.; Zou, G.; Capdevila, J. H. Tetrahedron Lett. 2001, 42, 7213-7215.
59. Höfle, G.; Glaser, N.; Leibold, T.; Sefkow, M. Pure Appl. Chem. 1999, 71, 2019-2024.
60. In the absence of water, starting aryl bromide 7 was recovered along with its homocoupling product in a 1:1 ratio.