Selective syntheses of mono- and diphosphanyltriazines as novel ligands for transition metal catalysts

European Journal of Organic Chemistry

Volumn , Issue 29, 2009, Pages 4956-4962

  Hayashi, Minoru ^a   Yamasaki, Toshikazu ^a   Kobayashi, Yusuke ^a   Imai, Yoshito ^a   Watanabe, Yutaka ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

Cross coupling; Nucleophilic substitution; P ligands; Phosphorus; Synthetic methods

Indexed keywords

EID: 70349769452     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900429     Document Type: Article

References (25)

1. a) M. L. Clarke, M. J. Williams, in: Organophosphorus Reagents (Ed.: P. J. Murphy), Oxford University Press, New York, 2004, chapter 2;
2. b) D. G. Gilheany, C. M. Mitchell, in: The Chemistry of Organophosphorus Compounds (Ed.: F. R. Hartley), John Wiley & Sons, Chichester, 1990, vol.1, p. 151-190.
3. a) G. Blotny, Tetrahedron 2006, 62, 9507-9522;
4. b) C. A. M. Afonso, N. M. T. Lourenço, A. A. Rosatella, Molecules 2006, 11, 81-102, and references cited therein.
5. For reviews, see: a) P. Gamez, J. Reedijk, Eur. J. Inorg. Chem. 2006, 29-42;
6. b) T. J. Mooibroek, P. Gamez, Inorg. Chim. Acta 2007, 360, 381-404.
7. B. Hoge, W. Wiebe, Angew. Chem. Int Ed. 2008, 47, 8116-8119.
8. The synthesis of phosphanyltriazines by capping all reactive sites in triazine derivatives with phosphane nucleophiles has been reported: a) W. Hewertson, R. A. Shaw, B. C. Smith, J. Chem. Soc. 1963, 1020-1026;
9. b) J. Zhang, M. Nieuwenhuyzen, J. P. H. Charmant, S. L. James, Chem. Commun. 2004, 2808;
10. c) P. W. Miller, M. Nieuwenhuyzen, S. L. James, CrystEngComm 2004, 68, 408-412;
11. d) M. Pietraszkiewicz, A. Klonkowski, K. Staniszewski, J. Karpiuk, S. Biankettia, J. Alloys Compd 2004, 380, 241. Only one example of mono-substitution has been reported:
12. e) J. McMurran, J. Kouvetakis, D. C. Nesting, J. L. Hubbard, Chem. Mater. 1998, 10, 590-593.
13. a) Y. Matsuura, T. Yamasaki, Y. Watanabe, M. Hayashi, Tetrahedron: Asymmetry 2007, 18, 2129-2132;
14. b) M. Hayashi, Y. Matsuura, T. Yamasaki, Y. Watanabe, J. Org. Chem. 2007, 72, 7798-7800;
15. c) M. Hayashi, Y. Matsuura, Y. Watanabe, J. Org. Chem. 2006, 71, 9248-9251;
16. d) M. Hayashi, Y. Matsuura, K. Kurihara, D. Maeda, Y. Nishimura, E. Morita, M. Okasaka, Y. Watanabe, Chem. Lett. 2007, 36, 634-635;
17. e) M. Hayashi, Y. Matsuura, Y. Watanabe, Tetrahedron Lett. 2005, 46, 5135-5138;
18. f) M. Hayashi, Y. Matsuura, Y. Watanabe, Tetrahedron Lett. 2004, 45, 9167-9169.
19. 2 (2.2 equiv.) caused degradation of the intermediate to give tetraphenyldiphosphane as a main product.
20. 3N reacted with the intermediates when used instead of DIPEA.
21. Complex formation of ligands with similar P-N and P-N-P substructure, where the N of the aromatic core is coordinated, have been reported: a) J. Zhang, P. W. Miller, M. Nieuwenhuyzen, S. L. James, Chem. Eur. J. 2006, 12, 2448-2453;
22. b) Q.-S. Li, C.-Q. Wan, F.-B. Xu, H.-B. Song, Z.-Z. Zhang, Inorg Chim. Acta 2005, 358, 2283-2291;
23. c) I. O. Koshevoy, M. Haukka, T. A. Pakkanen, S. P. Tunik, P. Vainiotalo, Organometallics 2005, 24, 3516-3526.
24. CCDC-719707 (for Pd-4a) and -719708 (for Pd-5c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
25. TONs were calculated from the reactions using 0.002 mol-% of Pd catalyst.