Highly chemoselective α-diazo carbonyl insertion reactions into N–H and S–H bonds catalysed by [RuCl(η⁵-C₅H₅)(PPh₃)₂]

Abstract

Complex [RuCl(η⁵-C₅H₅)(PPh₃)₂], in chloroform at 60 °C, catalyses the chemoselective insertion of α-diazo carbonyl compounds into N–H and S–H bonds to afford α-keto-amines and α-keto-thioethers.

References

1. M. P. Doyle, Chem. Rev., 1986, 86, 919; T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091; H. Zollinger, Diazo Chemistry II, Wiley, Weinheim, 1995; M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998, ch. 8.
2. Most recent papers: G. Emmer, Tetrahedron, 1992, 48, 7165; K.-Y. Ko, K.-I. Lee and W.-J. Kim, Tetrahedron Lett., 1992, 33, 6651; K. Burger, M. Rudolph and S. Fehn, Angew. Chem., Int. Ed. Engl., 1993, 32, 285; S. Hanessian, J.-M. Fu, J.-L. Chiara and R. Di Fabio, Tetrahedron Lett., 1993, 34, 4157; J. Podlech and D. Seebach, Helv. Chim. Acta, 1995, 78, 1238.
3. Most recent papers: Y. Landais and D. Planchenault, Synlett, 1995, 1191; M. C. Bagley, R. T. Buck, S. L. Hind, C. J. Moody and A. M. Z. Slawin, Synlett, 1996, 825; S. N. Osipov, N. Sewald, A. F. Kolomiets, A. V. Fokin and K. Burger, Tetrahedron Lett., 1996, 37, 615; E. Aller, R. T. Buck, M. J. Drysdale, L. Ferris, D. Haigh, C. J. Moody, N. D. Pearson and J. B. Sanghera, J. Chem. Soc., Perkin Trans. 1, 1996, 2879; C. Fernández García, M. A. McKervey and T. Ye, Chem. Commun., 1996, 1465; C. J. Moody, L. Ferris, D. Haigh and E. Swann, Chem. Commun., 1997, 2391; M. C. Bagley, R. T. Buck, S. L. Hind and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1998, 591; C. J. Moody and M. C. Bagley, J. Chem. Soc., Perkin Trans. 1, 1998, 601.
4. E. Galardon, P. Le Maux and G. Simonneaux, J. Chem. Soc., Perkin Trans. 1, 1997, 2455.
5. S. Sengupta, D. Dan and D. S. Darma, Tetrahedron Lett., 1996, 37, 8815.
6. W. Baratta, A. Del Zotto and P. Rigo, Chem. Commun., 1997, 2163.
7. W. Baratta, A. Del Zotto and P. Rigo, Organometallics, 1999, in press.