Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Thexylalkoxyborane as Hydroborating Agent for Alkenes and Alkynes

  • Published : 1996.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

In order to elucidate the effect of alkoxy substituent in thexylborane and hence establish their usefulness as hydroborating agent, reactions of alkenes and alkynes with thexylalkoxyborane (ThxBHOR; R=Et, i-Pr, i-Bu, sec-Bu, t-Bu, Ph) were investigated in detail. The reagents readily hydroborated alkenes and alkynes of various structural types at 25 ℃ in excellent regioselectivity. The selectivity increases consistently with increasing steric size of alkoxy substituent. Especially, the selectivity achieved by the sec-butoxy derivative is comparable to that previously achieved by thexylhaloborane-methyl sulfide (ThxBHX·SMe2), the most selective hydroborating agent known.

Keywords

References

  1. J. Am. Chem. Soc. v.84 Brown, H. C.;Moerikofer, A. W.
  2. Inorg. Chem. v.1 Brown, H. C.;Klender, G. U.
  3. J. Am. Chem. Soc. v.89 Brown, H. C.;Pfaffenberger, C. D.
  4. J. Am. Chem. Soc. v.89 Brown, H. C.;Negishi, E.
  5. Chem. Commun. Brown, H. C.;Negishi, E.
  6. J. Org. Chem. v.47 Brown, H. C.;Sikorski, J. A.;Kulkarni, S. V.;Lee, H. D.
  7. J. Org. Chem. v.47 Sikorski, J. A.;Brown, H. C.
  8. J. Org. Chem. v.102 Zweifel, G.;Person, N. R.
  9. Tetrahedron. Lett. v.34 Cha, J. S.;Min, S. J.;Kim, J. M.;Kwon, O. O.
  10. Bull. Korean Chem. Soc. v.15 Cha, J. S.;Min, S. J.;Kim, J. M.
  11. J. Org. Chem. v.45 Brown, H. C.;Sikorski, J. A.;Kulkarni, S. V.;Lee, H. D.
  12. J. Org. Chem. v.45 Kulkarni, S. V.;Lee, H. D.;Brown, H. C.
  13. Organomet. v.1 Brown, H. C.;Sikorski, J. A.
  14. Synthesis Brown, H. C.;Lee, H. D.;Kulkarni, S. V.
  15. Synthesis Kulkarni, S. V.;Lee, H. D.;Brown, H. C.
  16. Synthesis Brown, H. C.;Bhat, N. G.;Basavaiah, D.
  17. J. Org. Chem. v.51 Brown, H. C.;Nazer B.;Cha, J. S.;Sikorski, J. A.
  18. Bull. Korean Chem. Soc. v.8 Cha, J. S.;Kim, J. E.;Oh, S. Y.
  19. Org. Prep. Proced. Int. v.25 Cha, J. S.;Min, S. J.;Kim, J. M.;Kwon, O. O.;Jeoung, M. K.
  20. J. Am. Chem. Soc. v.106 Brown, H. C.;Cha, J. S.;Nazer, B.;Yoon, N. M.
  21. J. Org. Chem. v.52 Brown, H. C.;Cha, J. S.;Nazer, B.;Yoon, N. M.
  22. J. Org. Chem. v.52 Cha, J. S.;Kim, J. E.;Lee, K. W.
  23. Bull. Korean Chem. Soc. v.8 Cha, J. S.;Oh, S. Y.;Kim, J. E.
  24. Bull. Korean Chem. Soc. v.9 Cha, J. S.;Lee, K. W.;Yoon, M. S.;Lee. J. C.
  25. Org. Prep. Proced. Int. v.21 Cha, J. S.
  26. Bull. Korean Chem. Soc. v.7 Kim, G. P.;Yoon, N. M.
  27. J. Am. Chem. Soc. v.82 Brown, H. C.;Zweifel, G.
  28. J. Am. Chem. Soc. v.83 Brown, H. C.;Zweifel, G.
  29. Organomet. Chem. Synth. Plamondon, J.;Snow, J. T.;Zweifel, G.
  30. J. Org. Chem. v.45 Brown, H. C.;Campbell, J. B. Jr.
  31. J. Am. Chem. Soc. v.97 Brown, H. C.;Gupta, S. K.
  32. Heterocycles v.32 Cha, J. S.;Seo, J. B.;Lee, J. C.;Kim, J. M.;Lee, H. S.;Park, Y. B.;Uhm, J. K.;Shim, S. C.;Kim, H. S.;Kim, T. J.;Kwak, Y. W.;Lee, D. H.
  33. J. Am. Chem. Soc. v.101 Brown, H. C.;Scouten, C. G.;Liotta, R.
  34. Z. Natorforsch. v.146 Bartocha, B.;Douglas, C. M.;Gray, M. Y.
  35. Bull. Korean Chem. Soc. v.15 Cha, J. S.;Min, S. J.;Kim, J. M.
  36. Bull. Korean Chem. Soc. v.16 Cha, J. S.;Min, S. J.;Kim, J. M.;Kwon, O. O.;Kim, E. J.
  37. Organic Synthesis via Boranes Brown, H. C.;Kramer, G. W.;Levy, A. B.;Midland, M. M.
  38. J. Org. Chem. v.37 Brown, H. C.;Heim, P.;Yoon, N. M.
  39. J. Korean Chem. Soc. v.22 Yoon, N. M.;Cha, J. S.