Square-planar diacetatopalladium complexes with trans-configured secondary amine ligands that avoid orthometalation: Ligand synthesis, coordination, molecular structure and catalytic potential for Suzuki cross-coupling reactions

European Journal of Inorganic Chemistry

Volumn , Issue 32, 2007, Pages 5045-5051

  Chahen, Ludovic ^a   Therrien, Bruno ^a   Süss Fink, Georg ^a  

^a UNIVERSITÉ DE NEUCHÂTEL   (Switzerland)

Author keywords

Amines; Cross coupling; Homogeneous catalysis; N ligands; Palladium

Indexed keywords

AMINES; CATALYSIS; CHELATION; CRYSTAL ATOMIC STRUCTURE; LIGANDS; ORGANOMETALLICS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL);

AMINE LIGAND; CATALYTIC POTENTIAL; CROSS-COUPLINGS; HOMOGENEOUS CATALYSIS; N LIGANDS; N-LIGANDS; ORTHO-METALATION; PALLADIUM COMPLEXES; SECONDARY AMINES; SUZUKI CROSS COUPLING REACTIONS;

PALLADIUM COMPOUNDS;

EID: 36349025706     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200700518     Document Type: Article

References (33)

1. a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
2. b) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633;
3. c) A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90;
4. d) F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 15, 2419.
5. a) A. Zapf, M. Beller, Chem. Eur. J. 2001, 7, 908;
6. b) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem. Int. Ed. Engl. 1995, 34, 1848;
7. c) R. B. Bedford, S. L. Hazelwood (née Welch), M. E. Limmert, D. A. Albisson, S. M. Draper, P. N. Scully, S. J. Coles, M. B. Hursthouse, Chem. Eur. J. 2003, 9, 3216.
8. a) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685;
9. b) J. Yin, M. P. Rainka, X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162;
10. c) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550;
11. d) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. Int. Ed. 2004, 43, 1871.
12. a) B. Tao, D. W. Boykin, Tetrahedron Lett. 2002, 43, 4955;
13. b) D. A. Alonso, C. Najera, M. C. Pacheco, Org. Lett. 2000, 2, 1823;
14. c) L. Botella, C. Najera, Angew. Chem. Int. Ed. 2002, 41, 179;
15. d) H. Weissman, D. Milstein, Chem. Commun. 1999, 1901;
16. e) R. B. Bedford, C. S. Cazin, Chem. Commun. 2001, 1540;
17. f) G. A. Grasa, A. C. Hillier, S. P. Nolan, Org. Lett. 2001, 3, 1077.
18. a) B. Tao, D. W. Boykin, J. Org. Chem. 2004, 69, 4330;
19. b) B. Tao, D. W. Boykin, Tetrahedron Lett. 2003, 44, 7993.
20. L. Chahen, B. Therrien, G. Süss-Fink, J. Organomet. Chem. 2006, 691, 4257.
21. J. R. Miecznikowski, R. H. Crabtree, Polyhedron 2004, 23, 2857.
22. a) S. V. Kravtsova, I. P. Romm, A. I. Stash, V. K. Belsky, Acta Crystallogr., Sect. C 1996, 52, 2201;
23. b) S. Bouquillon, J. Rouden, J. Muzart, M.-C. Lasne, M. Hervieu, A. Leclaire, B. Tinant, C. R. Chim. 2006, 9, 1301.
24. J. C. Barnes, J. D. Paton, J. R. Damewood, K. Mislow, J. Org. Chem. 1981, 46, 4975.
25. W. E. Geiger, N. Van Order, D. T. Pierce, T. E. Bitterwolf, A. L. Rheingold, N. D. Chasteen, Organometallics 1991, 10, 2403.
26. A. Alimardanov, L. Schmieder-van de Vomdervoort, A. H. M. de Vries, Adv. Synth. Catal. 2004, 346, 1812.
27. J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662.
28. T. Brenstrum, D. A. Gerritsma, G. M. Adjabeng, C. S. Frampton, J. Britten, A. J. Robertson, J. McNulty, A. Capretta, J. Org. Chem. 2004, 69, 7635.
29. A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickz, J. G. de Vries, Org. Lett. 2003, 5, 3285.
30. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467.
31. G. M. Sheldrick, SHELXL-97, University of Göttingen, Germany, 1999.
32. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
33. I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor, Acta Crystallogr., Sect. B 2002, 58, 389.