A new germanium based linker for solid phase synthesis of aromatic compounds

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Alan C. Spivey, Christopher M. Diaper and Andrew J. Rudge


Abstract

An efficient three-step synthesis of germyl linker precursor 4 is described which enables a simple two step immobilisation of lithiated aromatics to Argogel™ polymer; cleavage from the polymer support via ipso-degermylation with TFA, ICl, Br2 and NCS provides protio-, iodo-, bromo- and chloro- aryls, respectively.


References

  1. B. B. Backes and J. A. Ellman, Curr. Opin. Chem. Biol., 1997, 1, 86 CrossRef CAS.
  2. Y. Hu, J. A. Porco, J. W. Labadie, O. W. Gooding and B. M. Trost, J. Org. Chem., 1998, 63, 4518 CrossRef CAS and references therein.
  3. C. J. Eaborn, J. Organomet. Chem., 1975, 100, 43 CrossRef CAS.
  4. Y. Han, S. D. Walker and R. N. Young, Tetrahedron Lett., 1996, 37, 2703 CrossRef CAS.
  5. A. Vasella and C. Cai, Helv. Chim. Acta, 1996, 79, 255 CrossRef.
  6. C. Dallaire and M. A. Brook, Organometallics, 1990, 9, 2873 CrossRef CAS.
  7. M. J. Plunkett and J. A. Ellman, J. Org. Chem., 1997, 62, 2885 CrossRef CAS.
  8. J. Satge, M. Massol and P. Riviere, J. Organomet. Chem., 1973, 56, 1 CrossRef CAS.
  9. V. F. Mironov and T. K. Gar, J. Gen. Chem. USSR (Engl. Transl.), 1975, 45, 94.
  10. S. P. Kolesnikov, B. L. Perl'mutter and O. M. Nefedov, Dokl. Chem. (Engl. Transl.), 1970, 196, 85.
  11. M. Lesbre, P. Mazerolles and J. Satge, The Organic Compounds of Germanium, ed. D. Seyferth, Wiley, 1973 Search PubMed.
  12. E. J. Bulten and W. Drenth, J. Organomet. Chem., 1973, 61, 179 CrossRef CAS.
  13. C. Eaborn and K. C. Pande, J. Chem. Soc., 1960, 3200 RSC.
  14. T. Tsunoda, J. Otsuka, Y. Yamamiya and S. Ito, Chem. Lett., 1994, 539 CAS.
  15. F. Ehrlich and P. Pistchimuka, Chem. Ber., 1912, 45, 2428 Search PubMed.
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