Synthesis of a new camphor derived P,S(O) ligand. the importance of C-H⋯O bonding in the ligand exchange reactions with Co 2(μ-alkyne)(CO)6 complexes

Journal of Organometallic Chemistry

Volumn 695, Issue 22, 2010, Pages 2377-2380

  Sol, Jordi ^a   Riera, Antoni ^a   Verdaguer, Xavier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

P,S ligands; Pauson Khand reaction; Sulfoxides; Weak hydrogen bonds

Indexed keywords

COBALT COMPLEXES; COORDINATION MODES; COORDINATION PROPERTIES; DICOBALT HEXACARBONYL; LIGAND EXCHANGE REACTIONS; METHINE GROUP; PAUSON-KHAND REACTIONS; S LIGANDS; SOLID-STATE STRUCTURES; SULFOXIDES; SULFUR ATOMS; WEAK HYDROGEN BOND; X-RAY STRUCTURE;

ACETYLENE; COBALT; COBALT COMPOUNDS; COMPLEXATION; HYDROGEN; HYDROGEN BONDS; LIGANDS; SULFUR; SYNTHESIS (CHEMICAL);

CHELATION;

DRYOBALANOPS;

EID: 84755161588     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.07.021     Document Type: Article

References (36)

1. E.N. Jacobsen, A. Pfatz, H. Yamamoto, Comprehensive Asymmetric Catalysis 1999 Springer Berlin
2. A. Borner, Phosphorus Ligands in Asymmetric Catalysis 2008 Wiley-VCH Weinheim
3. F.-L. Lam, F.-Y. Kwong, and A.S.C. Chan Chem. Commun. 46 2010 4649
4. I.U. Khand, G.R. Knox, P.L. Pauson, W.E. Watts, and M.I. Foreman J. Chem. Soc. Perkin Trans. 1. 1973 977
5. I.U. Khand, G.R. Knox, P.L. Pauson, and W.E. Watts J. Chem. Soc. Chem. Commun. 1971 36
6. For recent reviews about the Pauson-Khand reaction see:
7. H.-W. Lee, and F.-Y. Kwong Eur. J. Org. Chem. 2010 789
8. T. Shibata Adv. Synth. Catal. 348 2006 2328
9. D. Struebing, and M. Beller Top. Organomet. Chem. 18 2006 165
10. M.R. Rivero, J. Adrio, and J.C. Carretero Synlett 2005 26
11. S. Laschat, A. Becheanu, T. Bell, and A. Baro Synlett 2005 2547
12. S.E. Gibson, and N. Mainolfi Angew. Chem. Int. Ed. 44 2005 3022
13. L.V.R. Bonaga, and M.E. Krafft Tetrahedron 60 2004 9795
14. J. Blanco-Urgoiti, L. Anorbe, L. Perez-Serrano, G. Dominguez, and J. Perez-Castells Chem. Soc. Rev. 33 2004 32
15. S.E. Gibson, and A. Stevenazzi Angew. Chem. Int. Ed. 42 2003 1800
16. X. Verdaguer, A. Moyano, M.A. Perics, A. Riera, M.A. Maestro, and J. Mahia J. Am. Chem. Soc. 122 2000 10242
17. X. Verdaguer, M.A. Perics, A. Riera, M.A. Maestro, and J. Mahia Organometallics 22 2003 1868
18. J. Sol, M. Revés, A. Riera, and X. Verdaguer Angew. Chem. Int. Ed. 46 2007 5020
19. M. Revés, T. Achard, J. Sol, A. Riera, and X. Verdaguer J. Org. Chem. 73 2008 7080
20. Y. Ji, A. Riera, and X. Verdaguer Org. Lett. 11 2009 4346
21. C. Ferrer, A. Riera, and X. Verdaguer Organometallics 28 2009 4571
22. J. Sol, A. Riera, X. Verdaguer, and M.A. Maestro J. Am. Chem. Soc. 127 2005 13629
23. J. Sol, A. Riera, X. Verdaguer, and M.A. Maestro Organometallics 25 2006 5795
24. X. Verdaguer, A. Lledó, C. Lopez-Mosquera, M.A. Maestro, M.A. Perics, and A. Riera J. Org. Chem. 69 2004 8053
25. M. Iqbal, P. Evans, A. Lledó, X. Verdaguer, M.A. Perics, A. Riera, C. Loeffler, A.K. Sinha, and M.J. Mueller ChemBioChem 6 2005 276
26. A. Vázquez-Romero, J. Rodriguez, A. Lledó, X. Verdaguer, and A. Riera Org. Lett. 10 2008 4509
27. M. Iqbal, P. Duffy, P. Evans, G. Cloughley, B. Allan, A. Lledó, X. Verdaguer, and A. Riera Org. Biomol. Chem. 6 2008 4649
28. A. Vázquez-Romero, L. Cárdenas, E. Blasi, X. Verdaguer, and A. Riera Org. Lett. 11 2009 3104
29. V.K. Aggarwal, R. Angelaud, D. Bihan, P. Blackburn, R. Fieldhouse, S.J. Fonquerna, G.D. Ford, G. Hynd, E. Jones, R.V.H. Jones, P. Jubault, M.J. Palmer, P.D. Ratcliffe, and H. Adams J. Chem. Soc. 2001 2604
30. B.H. Schlessinger, and A. Lopes J. Org. Chem. 46 1981 5253
31. D. Braga, F. Grepioni, and G.R. Desiraju Chem. Rev. 98 1998 1375
32. F.A. Cotton, and R. Francis J. Am. Chem. Soc. 82 1960 2986
33. F.A. Cotton, R. Francis, and W.D. Horrocks J. Phys. Chem. 64 1960 1534
34. Oxygen coordination to cobalt hexacarbonyl complexes employing N-phosphinosulfinamide or sulfinylmethylphosphine ligands has never been observed in our group. See Ref. [5] for details.
35. X. Verdaguer, A. Moyano, M.A. Perics, A. Riera, A. Alvarez-Larena, and J.-F. Piniella Organometallics 18 1999 4275
36. Unfortunately Pauson-Khand reaction of complex 4 with norbornadiene did not provided the expected cyclopentenone. Internal alkynes are much less reactive than the terminal ones (see Ref. [5c]). The presence of bulky tert-butylsulfony groups attached to the alkyne prevents olefin insertion in compound 4.