View PDF Version
 
DOI: 10.1039/A800108A (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1998, 1431-1438

Platinum-catalysed 1,4-diboration of 1,3-dienes

(Note: The full text of this document is currently only available in the PDF Version )

William Clegg, Thorsten R. F. Johann, Todd B. Marder, Nicholas C. Norman, A. Guy Orpen, Torren M. Peakman, Michael J. Quayle, Craig R. Rice and Andrew J. Scott

Abstract

The chiral diborane(4) compounds B2[R,R-O2CH(CO2Me)CH(CO2Me)]2, B2(S-O2CH2CHPh)2, B2(R,R-O2CHPhCHPh)2 and B2(O2C20H12)2 (O2C20H12 = 1,7′-bi-2-naphtholate) have been synthesized. All four compounds have been characterised by X-ray crystallography, the latter as a racemate. The B–B bond oxidative-addition reactions of the first three compounds with [Pt(PPh3)2(η-C2H4)] resulted in the platinum(II) bis(boryl) complexes cis-[Pt(PPh3)2{B[R,R-O2CH(CO2Me)CH(CO2Me)]}2], cis-[Pt(PPh3)2{B(S-O2CH2CHPh)}2] and cis-[Pt(PPh3)2{B(R,R-O2CHPhCHPh)}2]; the former two were also characterised by X-ray crystallography. The platinum-catalysed diborations of a range of prochiral 1,3-dienes with the compounds B2[R,R-O2CH(CO2Me)CH(CO2Me)]2, B2(S-O2CH2CHPh)2 and B2(R,R-O2CHPhCHPh)2 were studied. Although these reactions were clean and quantitative, observed product d.e.s (measured by 1H NMR spectroscopy) were low or non-existent indicating that chirality transfer from the diborane(4) diolate groups to the diene diboration product is not efficient in these cases.

References

  1. T. Ishiyama, M. Yamamoto and N. Miyaura, Chem. Commun., 1997, 689 RSC; C. N. Iverson and M. R. Smith, Organometallics, 1997, 16, 2757 CrossRef CAS.
  2. (a) T. Ishiyama, N. Matsuda, N. Miyaura and A. Suzuki, J. Am. Chem. Soc., 1993, 115, 11 018 CrossRef CAS; (b) T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki and N. Miyaura, Organometallics, 1996, 15, 713 CrossRef; (c) C. N. Iverson and M. R. Smith, J. Am. Chem. Soc., 1995, 117, 4403 CrossRef CAS; (d) C. N. Iverson and M. R. Smith, Organometallics, 1996, 15, 5155 CrossRef CAS; (e) G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg and N. C. Norman, Organometallics, 1996, 15, 5137 CrossRef; (f) A. Maderna, H. Pritzkow and W. Siebert, Angew. Chem., Int. Ed. Engl., 1995, 35, 1501 CrossRef CAS.
  3. T. Ishiyama, M. Yamamoto and N. Miyaura, Chem. Commun., 1996, 2073 RSC.
  4. Y. G. Lawson, M. J. G. Lesley, T. B. Marder, N. C. Norman and C. R. Rice, Chem. Commun., 1997, 2051 RSC.
  5. S. Sakaki and T. Kikuno, Inorg. Chem., 1997, 36, 226 CrossRef CAS; Q. Cui, D. G. Musaev and K. Morokuma, Organometallics, 1997, 16, 1355 CrossRef CAS.
  6. W. Clegg, F. J. Lawlor, G. Lesley, T. B. Marder, N. C. Norman, A. G. Orpen, M. J. Quayle, C. R. Rice, A. J. Scott and F. E. S. Souza, J. Organomet. Chem., in the press Search PubMed.
  7. A. Kerr, T. B. Marder, N. C. Norman, A. G. Orpen, M. J. Quayle, C. R. Rice, P. L. Timms and G. R. Whittell, Chem. Commun., 1998, 319 RSC.
  8. H. Wadepohl, Angew. Chem., Int. Ed. Engl., 1997, 36, 2441 CrossRef CAS; T. B. Marder and N. C. Norman, Top. Catalysis, eds. W. Leitner and D. G. Blackmond, Baltzer Science Publishers, Amsterdam, 1998, in the press Search PubMed; G. J. Irvine, M. J. G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, E. G. Robins, W. R. Roper and G. R. Whittell, Chem. Rev., submitted Search PubMed.
  9. T. B. Marder, N. C. Norman and C. R. Rice, Tetrahedron Lett., 1998, 39, 155 CrossRef CAS.
  10. F. J. Lawlor, N. C. Norman, N. L. Pickett, E. G. Robins, P. Nguyen, G. Lesley, T. B. Marder, J. A. Ashmore and J. C. Green, Inorg. Chem., in the press Search PubMed.
  11. W. Clegg, M. R. J. Elsegood, F. J. Lawlor, N. C. Norman, N. L. Pickett, E. G. Robins, A. J. Scott, P. Nguyen, N. J. Taylor and T. B. Marder, Inorg. Chem., in the press Search PubMed.
  12. H. Nöth, Z. Naturforsch., Teil B, 1984, 39, 1463 Search PubMed.
  13. G. Lesley, T. B. Marder, N. C. Norman and C. R. Rice, Main Group Chem. News, 1997, 5, 4 Search PubMed.
  14. K. Burgess and M. J. Ohlmeyer, Chem. Rev., 1991, 91, 1179 CrossRef CAS; K. Burgess and W. A. van der Donk, Encyclopedia of Inorganic Chemistry, ed. R. B. King, Wiley, Chichester, 1994, vol. 3, p. 1420 Search PubMed; G. C. Fu, D. A. Evans and A. R. Muci, Advances in Catalytic Processes, ed. M. P. Doyle, JAI Press, Greenwich, CT, 1995, pp. 95–121 Search PubMed; I. Beletskaya and A. Pelter, Tetrahedron, 1997, 53, 4957 Search PubMed.
  15. R. J. Brotherton, J. L. McCloskey, L. L. Petterson and H. Steinberg, J. Am. Chem. Soc., 1960, 82, 6242 CrossRef CAS.
  16. M. Camalli, F. Caruso, S. Chaloupka, E. M. Leber, H. Rimml and L. M. Venanzi, Helv. Chim. Acta, 1990, 73, 2263 CrossRef CAS.
  17. B. H. McKee, D. G. Gilheany and K. B. Sharpless, Org. Synth., 1992, 70, 47 CAS.
  18. H. D. Flack, Acta Crystallogr., Sect. A, 1983, 39, 876 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.