New Pd-catalyzed tandem cyclization processes on group 6 bis-carbene complexes

Chemical Communications

Volumn , Issue 17, 2002, Pages 1842-1843

  Sierra, Miguel A ^a   Del Amo, Juan C ^a   Mancheño, María J ^a   Gómez Gallego, Mar ^a   Rosario Torres, M ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

EID: 0036971977     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b204907d     Document Type: Article

References (21)

1. Reviews dealing with different aspects of cascade processes in Cr-carbene complexes: (a) R. Aumann and H. Nienaber, Adv. Organomet. Chem., 1997, 41, 163; (b) A. de Meijere, H. Schirmer and M. Duetsch, Angew. Chem., Int. Ed., 2000, 39, 3964; (c) D. F. Harvey and D. M. Sigano, Chem. Rev., 1996, 96, 271; (d) In addition, for selected reviews on the chemistry of group 6 metal-carbene complexes, see: K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissel, U. Schuber and K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Deerfield Beach, Florida, 1983; (e) K. H. Dötz, Angew. Chem., Int. Ed. Engl., 1984, 23, 587; (f) W. D. Wulff, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 470; (g) L. S. Hegedus, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 549.
2. Reviews dealing with different aspects of cascade processes in Cr-carbene complexes: (a) R. Aumann and H. Nienaber, Adv. Organomet. Chem., 1997, 41, 163; (b) A. de Meijere, H. Schirmer and M. Duetsch, Angew. Chem., Int. Ed., 2000, 39, 3964; (c) D. F. Harvey and D. M. Sigano, Chem. Rev., 1996, 96, 271; (d) In addition, for selected reviews on the chemistry of group 6 metal-carbene complexes, see: K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissel, U. Schuber and K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Deerfield Beach, Florida, 1983; (e) K. H. Dötz, Angew. Chem., Int. Ed. Engl., 1984, 23, 587; (f) W. D. Wulff, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 470; (g) L. S. Hegedus, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 549.
3. Reviews dealing with different aspects of cascade processes in Cr-carbene complexes: (a) R. Aumann and H. Nienaber, Adv. Organomet. Chem., 1997, 41, 163; (b) A. de Meijere, H. Schirmer and M. Duetsch, Angew. Chem., Int. Ed., 2000, 39, 3964; (c) D. F. Harvey and D. M. Sigano, Chem. Rev., 1996, 96, 271; (d) In addition, for selected reviews on the chemistry of group 6 metal-carbene complexes, see: K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissel, U. Schuber and K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Deerfield Beach, Florida, 1983; (e) K. H. Dötz, Angew. Chem., Int. Ed. Engl., 1984, 23, 587; (f) W. D. Wulff, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 470; (g) L. S. Hegedus, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 549.
4. Reviews dealing with different aspects of cascade processes in Cr-carbene complexes: (a) R. Aumann and H. Nienaber, Adv. Organomet. Chem., 1997, 41, 163; (b) A. de Meijere, H. Schirmer and M. Duetsch, Angew. Chem., Int. Ed., 2000, 39, 3964; (c) D. F. Harvey and D. M. Sigano, Chem. Rev., 1996, 96, 271; (d) In addition, for selected reviews on the chemistry of group 6 metal-carbene complexes, see: K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissel, U. Schuber and K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Deerfield Beach, Florida, 1983; (e) K. H. Dötz, Angew. Chem., Int. Ed. Engl., 1984, 23, 587; (f) W. D. Wulff, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 470; (g) L. S. Hegedus, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 549.
5. Reviews dealing with different aspects of cascade processes in Cr-carbene complexes: (a) R. Aumann and H. Nienaber, Adv. Organomet. Chem., 1997, 41, 163; (b) A. de Meijere, H. Schirmer and M. Duetsch, Angew. Chem., Int. Ed., 2000, 39, 3964; (c) D. F. Harvey and D. M. Sigano, Chem. Rev., 1996, 96, 271; (d) In addition, for selected reviews on the chemistry of group 6 metal-carbene complexes, see: K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissel, U. Schuber and K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Deerfield Beach, Florida, 1983; (e) K. H. Dötz, Angew. Chem., Int. Ed. Engl., 1984, 23, 587; (f) W. D. Wulff, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 470; (g) L. S. Hegedus, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 549.
6. Reviews dealing with different aspects of cascade processes in Cr-carbene complexes: (a) R. Aumann and H. Nienaber, Adv. Organomet. Chem., 1997, 41, 163; (b) A. de Meijere, H. Schirmer and M. Duetsch, Angew. Chem., Int. Ed., 2000, 39, 3964; (c) D. F. Harvey and D. M. Sigano, Chem. Rev., 1996, 96, 271; (d) In addition, for selected reviews on the chemistry of group 6 metal-carbene complexes, see: K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissel, U. Schuber and K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Deerfield Beach, Florida, 1983; (e) K. H. Dötz, Angew. Chem., Int. Ed. Engl., 1984, 23, 587; (f) W. D. Wulff, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 470; (g) L. S. Hegedus, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 549.
7. Reviews dealing with different aspects of cascade processes in Cr-carbene complexes: (a) R. Aumann and H. Nienaber, Adv. Organomet. Chem., 1997, 41, 163; (b) A. de Meijere, H. Schirmer and M. Duetsch, Angew. Chem., Int. Ed., 2000, 39, 3964; (c) D. F. Harvey and D. M. Sigano, Chem. Rev., 1996, 96, 271; (d) In addition, for selected reviews on the chemistry of group 6 metal-carbene complexes, see: K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissel, U. Schuber and K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Deerfield Beach, Florida, 1983; (e) K. H. Dötz, Angew. Chem., Int. Ed. Engl., 1984, 23, 587; (f) W. D. Wulff, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 470; (g) L. S. Hegedus, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 549.
8. (a) K. H. Dötz, Angew. Chem., Int. Ed., 1975, 14, 644;
9. (b) K. H. Dötz, J. Organomet. Chem., 1977, 140, 177.
10. (a) M. A. Sierra, M. J. Mancheño, E. Sáez and J. C. del Amo, J. Am. Chem. Soc., 1998, 120, 6812;
11. (b) M. A. Sierra, J. C. del Amo, M. J. Mancheño and M. Gómez-Gallego, J. Am. Chem. Soc., 2001, 123, 851.
12. H. Sakurai, K. Tanabe and K. Narasaka, Chem. Lett., 1999, 75.
13. (a) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich and O. Meyer, Eur. J. Org. Chem., 1999, 64, 2545;
14. (b) I. Göttker-Schnetmann and R. Aumann, Organometallics, 2001, 20, 346.
15. J. Barluenga, L. A. López, O. Löber, M. Tomás, S. García-Granda, C. Alvarez-Rúa and J. Borge, Angew. Chem., Int. Ed., 2001, 40, 3392.
16. For a review on the preparation and chemistry of this kind of complexes, see: M. A. Sierra, Chem. Rev., 2000, 100, 3591.
17. (a) R. Aumann, R. Fröhlich and S. Kotila, Organometallics, 1996, 15, 4842;
18. (b) J. M. Moretó, S. Ricart, K. H. Dötz and E. Molins, Organometallics, 2001, 20, 62.
19. 4: Calcd C 78.85, H 6.14. Found: C 79.06, H 6.32%.
20. -1, F(000) = 1664. 10720 measured reflections were collected on a SMART CCD-BRUKER diffractometer, 3682 independent reflections (Rint = 0.0637), 290 refined parameters, final R indices [I > 3σ(I)], R1 = 0.0468, wR2 = 0.0945. CCDC 167018. See http://www.rsc.org/suppdata/cc/b2/b204907d/ for crystallographic files in CIF or other electronic format.
21. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley California, USA, 1987.