Polymer supported cobalt carbonyl complexes as novel traceless alkyne linkers for solid-phase synthesis

Abstract

The immobilisation of functionalised alkynes onto ‘polymer-bound triphenylphosphine’, their chemical manipulation and subsequent release has been demonstrated for the first time, thus illustrating that cobalt carbonyl complexes can be used as ‘traceless’ π-alkyne linkers.

References

1. A. R. Brown, P. H. H. Hermkens, H. C. J. Ottenheijm and D. C. Rees, Synlett, 1998, 817.
2. F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky and C. Zechel, Angew. Chem., Int. Ed. Engl., 1996, 35, 2288.
3. P. H. H. Hermkens, H. C. J. Ottenheijm and D. C. Rees, Tetrahedron Report No. 418, Tetrahedron, 1997, 53, 5643.
4. M. J. Plunkett and J. A. Ellman, J. Org. Chem., 1997, 62, 2885.
5. S. E. Gibson (née Thomas), N. J. Hales and M. A. Peplow, Tetrahedron Lett., 1999, 40, 1417.
6. Alkynes have been immobilised via Michael addition but are liberated as enones, N. W. Hird, K. Irie and K. Nagai, Tetrahedron Lett., 1997, 38, 7111 or ketones, N. W. Hird, M. Crawshaw, K. Irie and K. Nagai, Tetrahedron Lett., 1997, 38, 7115 and the cyclocondensation of acetylenic ketones with a resin-bound thiouronium salt has generated pyrimidine heterocycles, D. Obrecht, C. Abrecht, A. Grieder and J. M. Villalgordo, Helv. Chim. Acta., 1997, 80, 65.
7. (a) K. M. Nicholas and R. Pettit, Tetrahedron Lett., 1971, 3475; (b) T. Nakamura, T. Matsui, K. Tanino and I. Kawajima, J. Org. Chem., 1997, 62, 3032; (c) For a recent review of the asymmetric reaction: O. Geis and H. G. Schmaltz, Angew. Chem., Int. Ed., 1998, 37, 911.
8. R. A. Dubois, P. E. Garrou, K. D. Lavin and H. R. Allcock, Organometallics, 1986, 5, 460.
9. C. De-An and C. U. Pittman Jr., J. Mol. Catal., 1983, 21, 405.
10. A. J. Poe, J. Organomet. Chem., 1975, 94, 235.
11. For a representative monophosphine derivative see: G. Váradi, A. Vizi-Orosz, S. Vastag and G. Pályi, J. Organomet. Chem., 1976, 108, 225 and for a bisphosphine derivative see M. F. D'Agostino, C. S. Frampton and M. J. McGlinchey, Organometallics, 1990, 9, 2972.
12. A. M. Fivush and T. M. Willson, Tetrahedron Lett., 1997, 38, 7151.