Diastereopure cationic NCN-pincer palladium complexes with square planar η4-N,C,N,O coordination

European Journal of Inorganic Chemistry

Volumn , Issue 22, 2006, Pages 4600-4607

  Gosiewska, Silvia ^a   Martinez, Sara Herreras ^a   Lutz, Martin ^b   Spek, Anthony L ^b   Van Koten, Gerard ^a   Gebbink, Robertus J M Klein ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Amino acids; Hydrogen bonds; Ligand design; NCN pincer; Palladium

Indexed keywords

COMPLEX NETWORKS; COMPLEXATION; CONDENSATION REACTIONS; CRYSTAL STRUCTURE; KETONES; LIGANDS; MOLECULES; PALLADIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMINO-ACIDS; BROMIDE IONS; CATIONIC COMPLEXES; CATIONICS; ENANTIOPURE; LIGAND DESIGN; NCN PINCER PALLADIUM COMPLEXES; NCN-PINCER; PINCER LIGANDS; SYNTHESISED;

HYDROGEN BONDS;

EID: 33845312269     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600508     Document Type: Article

References (53)

1. For reviews on pincer complexes, see a) M. Albrecht, G. van Koten, Angew. Chem. Int. Ed. 2001, 40, 3750-3781;
2. b) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759-1792;
3. c) J. T. Singleton, Tetrahedron 2003, 59, 1837-1857;
4. for a general review on palladacycles, see d) J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527-2571.
5. For the NCN-pincer complexes, see a) J. G. Donkervoort, J. L. Vicario, J. T. B. H. Jastrzebski, W. J. J. Smeets, A. L. Spek, G. van Koten, J. Organomet. Chem. 1998, 551, 1-7;
6. b) M. Albrecht, B. M. Kocks, A. L. Spek, G. van Koten, J. Organomet. Chem. 2001, 624, 271-286;
7. c) E. Diez-Barra, J. Guerra, I. Lopez-Solera, S. Merino, J. Rodrigues-Lopez, P. Sanchez-Verdu, J. Tejeda, Organometallics 2003, 22, 541-547.
8. For the PCP complexes see a) F. Gorla, A. Togni, L. M. Venanzi, A. Albinati, F. Lianza, Organometallics 1994, 13, 1607-1616;
9. b) J. M. Longmire, X. Zhang, Tetrahedron Lett. 1997, 38, 1725-1728;
10. c) J. M. Longmire, X. Zhang, M. Shang, Organometallics 1998, 17, 4374-4379;
11. d) P. Dani, M. Albrecht, G. P. M. van Klink, G. van Koten, Organometallics 2000, 19, 4468-4476.
12. For the NCN-pincer complexes, see a) J. A. M. van Beek, G. van Koten, M. J. Ramp, N. C. Coenjaarts, D. Grove, K. Goubitz, M. C. Zoutberg, C. H. Stam, W. J. J. Smeets, A. L. Spek, Inorg. Chem. 1991, 30, 3059-3068;
13. b) L. van Kuil, Y. S. J. Veldhuizen, D. Grove, J. W. Zwikker, J. W. Jenneskens, W. Drenth, W. J. J. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pays-Bas 1994, 113, 267-277;
14. c) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715-4720.
15. For the Phebox-pincer complexes, see a) Y. Motoyama, N. Makihara, Y. Mikami, K. Aoki, H. Nishiyama, Chem. Lett. 1997, 951-952;
16. b) S. E. Denmark, R. A. Stavenger, A.-M. Faucher, J. P. Edwards, J. Org. Chem. 1997, 62, 3375-3389;
17. c) M. A. Stark, C. J. Richards, Tetrahedron Lett. 1997, 38, 5881-5884;
18. d) Y. Motoyama, Y. Mikami, H. Kawakami, K. Aoki, H. Nishiyama, Organometallics 1999, 18, 3584-3588;
19. e) Y. Motoyama, H. Narusawa, H. Nishiyama, Chem. Commun. 1999, 131-132;
20. f) M. A. Stark, G. Jones, C. J. Richards, Organometallics 2000, 19, 1282-1291;
21. g) M. Gerisch, J. R. Krumper, R. G. Bergman, T. D. Tilley, J. Am. Chem. Soc. 2001, 123, 5818-5819;
22. h) Y. Motoyama, M. Okano, H. Narusawa, N. Makihara, K. Aoki, H. Nishiyama, Organometallics 2001, 20, 1580-1591;
23. i) Y. Motoyama, Y. Koga, H. Nishiyama, Tetrahedron 2001, 57, 853-860;
24. j) Y. Motoyama, K. Shimozono, K. Aoki, H. Nishiyama, Organometallics 2002, 21, 1684-1694;
25. k) Y. Motoyama, H. Kawakami, K. Shimozono, K. Aoki, H. Nishiyama, Organometallics 2002, 21, 3408-3416;
26. l) Y. Motoyama, Y. Koga, K. Kobayashi, K. Aoki, H. Nishiyama, Chem. Eur. J. 2002, 8, 2968-2975;
27. m) M. Gerisch, J. R. Krumper, R. G. Bergman, T. D. Tilley, Organometallics 2003, 22, 47-58;
28. n) H. Nishiyama, T. Shiomi, Y. Tsuchiya, I. Matsuda, J. Am. Chem. Soc. 2005, 127, 6972-6973.
29. For the PCP complexes, see a) B. S. Wiliams, P. Dani, M. Lutz, A. L. Spek, G. van Koten, Helv. Chim. Acta 2001, 84, 3519-3530;
30. b) D. Morales-Morales, R. E. Cramer, C. M. Jensen, J. Organomet. Chem. 2002, 654, 44-50;
31. c) S. Medici, M. Gagliardo, B. S. Williams, P. A. Chase, S. Gladiali, M. Lutz, A. L. Spek, G. P. M. van Klink, G. van Koten, Helv. Chim. Acta 2005, 88, 694-705.
32. For the SCS-pincer complexes, see D. R. Evans, M. Huang, W. M. Seganish, J. C. Fettinger, T. L. Williams, Organometallics 2002, 21, 893-900.
33. a) K. Takenaka, Y. Uozumi, Org. Lett. 2004, 6, 1833-1835;
34. b) K. Takenaka, Y. Uozumi, Adv. Synth. Catal. 2004, 346, 1693-1696;
35. c) K. Takenaka, M. Minakawa, Y. Uozumi, J. Am. Chem. Soc. 2005, 127, 12273-12281.
36. S. Gosiewska, M. Huis in't Veld, J. J. M. de Pater, P. C. A. Bruijnincx, M. Lutz, A. L. Spek, R. J. M. Klein Gebbink, G. van Koten, Tetrahedron: Asymmetry 2006, 17, 674-686.
37. H. D. Flack, Acta Crystallogr., Sect. A 1983, 39, 876-881.
38. a) M. A. Stark, G. Jones, C. J. Richards, Organometallics 2000, 19, 1282-1291;
39. b) Y. Motoyama, K. Shimozono, K. Aoki, H. Nishiyama, Organometallics 2002, 21, 1684-1694;
40. c) J. van den Broeke, J. J. H. Heeringa, A. V. Chuchuryukin, H. Kooijman, A. M. Mills, A. L. Spek, J. H. van Lenthe, P. J. A. Ruttink, B.-J. Deelman, G. van Koten, Organometallics 2004, 23, 1287-1294.
41. J. Vicente, A. Arcas, Coord. Chem. Rev. 2005, 249, 1135-1154.
42. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
43. C) configurations are superimposable upon 180° rotation around the C-Pd axis and are therefore identical].
44. S. Gosiewska, S. Herreras Martinez, M. Lutz, A. L. Spek, R. W. A. Havenith, G. P. M. van Klink, G. van Koten, R. J. M. Klein Gebbink, manuscript in preparation.
45. N. C. Mehendale, R. J. M. Klein Gebbink, G. van Koten, manuscript in preparation.
46. a) Tris(δ,δ-dicampholylmethanato)europium(III): M. D. McCreary, D. W. Lewis, D. L. Wernick, G. M. Whitesides, J. Am. Chem. Soc. 1974, 96, 1038-1054;
47. b) Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405-6406.
48. D. Enders, P. Fey, H. Kipphardt, Organic Syntheses (Ed.: J. P. Freeman), Wiley, New York, 1993, vol. 8, p. 26.
49. C. H. M. Amijs, G. P. M. van Klink, G. van Koten, Green Chem. 2003, 5, 470-474.
50. S. Komiya (Ed.), Synthesis of Organometallic Compounds, Wiley, Chichester, U. K., 1997.
51. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla, The DIRDIF99 Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1999.
52. G. M. Sheldrick, SHELXS-97, Program for crystal structure solution, University of Göttingen, Germany, 1997.
53. G. M. Sheldrick, SHELXL-97, Program for crystal structure refinement, University of Göttingen, Germany, 1997.