Formation of unusual trinuclear assemblies: Scope and mechanism of Zn(salphen)-templated activation of pyridine-alcohol substrates

European Journal of Inorganic Chemistry

Volumn , Issue 35, 2009, Pages 5307-5318

  Belmonte, Marta Martínez ^a   Escudero Adán, Eduardo C ^a   Benet Buchholz, Jordi ^a   Kleij, Arjan W ^a,b  

^a INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

Salen; Self assembly; Supramolecular chemistry; Template effect; Zinc

Indexed keywords

ASSEMBLY; CHEMICAL ACTIVATION; COORDINATION REACTIONS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY; X RAY DIFFRACTION; ZINC COMPOUNDS;

OH-GROUPS; PROPERTY; SALEN; SELECTIVE ACTIVATION; SUPRAMOLECULAR ASSEMBLIES; TEMPLATE EFFECTS; TEMPLATED; TEMPLATING; TRINUCLEAR; ZINC;

SUPRAMOLECULAR CHEMISTRY;

EID: 72949123043     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200900862     Document Type: Article

References (48)

1. X. Li, D. R. Liu, Angew. Chem. Int. Ed. 2004, 43, 4848-4870.
2. For some recent examples, see: a) N. A. J. M. Sommerdijk, G. de With, Chem. Rev. 2008, 108, 4499-4550.
3. b) L. A. Wessjohann, D. G. Rivera, O. E. Vercillo, Chem. Rev. 2009, 109, 796-814.
4. c) J. D. Crowley, S. M. Goldup, A.-L. Lee, D. A. Leigh, R. T. McBurney, Chem. Soc. Rev. 2009, 38, 1530-1541.
5. V. Aucagne, K. D. Hänni, D. A. Leigh, P.J. Lusby, D. B. Walker, J. Am. Chem. Soc. 2006, 128, 2186-2187.
6. a) C. W. Toniøe, C., Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
7. b) V. V. Rostovtsev, L. G. Green, V.V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
8. V Aucagne, J. Berná, J. D. Crowley, S. M. Goldup, K. D. Hänni, D. A. Leigh, P. J. Lusby, V. E. Ronaldson, A. M. Z. Slawin, A. Viterisi, D. B. Walker, J. Am. Chem. Soc. 2007, 129, 11950-11963.
9. A. W. Kleij, Chem. Eur. J. 2008, 14, 10520-10529.
10. For some selected reviews, see: a) E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431.
11. b) P. G. Cozzi, Chem. Soc. Rev. 2004, 33, 410-421.
12. c) E. M. McGarrigle, D. G. Gilheany, Chem. Rev. 2005, 105, 1563-1602.
13. d) S. J. Wezenberg, A. W. Kleij, Angew. Chem. Int. Ed. 2008, 47, 2354-2364.
14. e) T. Katsuki, Chem. Soc. Rev. 2004, 33, 437-444;
15. C. Baleizão, H. Garcia, Chem. Rev. 2006, 106, 3987-4043.
16. a) P. D. Frischmann, A. J. Gallant, J. H. Chong, M. J. MacLachlan, Inorg. Chem. 2008, 47, 101-112.
17. b) G. Li, W. Yu, J. Ni, T. Liu, Y. Liu, E. Sheng, Y. Cui, Angew. Chem. Int. Ed. 2008, 47, 1245-1249.
18. c) S. Akine, S. Kagiyama, T. Nabeshima, Inorg. Chem. 2007, 46, 9525-9527.
19. d) A. W Kleij, M. Kuil, D. M. Tooke, A. L. Spek, J. N. H. Reek, Inorg. Chem. 2007, 46, 5829-5831.
20. a) A. J. Gallant, M. J. MacLachlan, Angew. Chem. Int. Ed. 2003, 42, 5307-5310.
21. b) S. J. Wezenberg, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Inorg. Chem. 2008, 47, 2925-2927.
22. c) J. K.-H. Hui, Z. Yu, M. J. MacLachlan, Angew. Chem. Int. Ed. 2007, 46, 7980-7983.
23. a) M. Kuil, P.E. Goudriaan, P. W N. M. Van Leeuwen, J.N.H. Reek, Chem. Commun. 2006, 4679-4681.
24. b) M. Kuil, P. E. Goudriaan, A. W Kleij, D. M. Tooke, A. L. Spek, P. W. N. M. van Leeuwen, J. N. H. Reek, Dalton Trans. 2007, 2311-2320.
25. c) H. Zelder, J. Rebek Jr, Chem. Commun. 2006, 753-754.
26. a) A. W Kleij, Eur. J. Inorg. Chem. 2009, 193-205.
27. b) S. Curreli, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, J. Org. Chem. 2007, 72, 7018-7021.
28. c) A. W. Kleij, D.M. Tooke, M. Lutz, A. L. Spek, I N H. Reek, Eur. J. Inorg. Chem. 2005, 4626-4634.
29. E. C. Escudero-Adán, J. Benet-Buchholz, A.W. Kleij, Inorg. Chem. 2008, 47, 410-412.
30. For selected examples of Zn(salen)-mediated catalytic conversions, see: a) B. Saito, T. Katsuki, Synlett 2004, 1557-1560.
31. b) P. G. Cozzi, Angew. Chem. Int. Ed, 2003, 42, 2895-2898.
32. c) Y.M. Shen, W.-L. Duan, M. Shi, J. Org. Chem. 2003, 68, 1559-1562.
33. The Lewis acidity of the Zn ion in salphen complexes is imparted by the unfavourable square-planar geometry posed by the salphen ligand. For structural and reactivity features by using these Lewis acidic Zn complexes, see: a) E. C. EscuderoAdán, J. Benet-Buchholz, A. W. Kleij, Chem. Eur. J. 2009, 15, 4233-4237.
34. b) S. J. Wezenberg, E. C. Escudero-Adán, J. BenetBuchholz, A. W. Kleij, Org. Lett. 2008, 10, 3311-3314.
35. 3.
36. 2 was previously reported. This structure has two saccharinate (sac) counter anions and comprises two neutral dmpy ligands; see: V. T. Yilmaz, S. Guney, O. Andac, W T. A. Harrison, J. Coord. Chem. 2003, 56, 21-32.
37. For related interactions between anions and Zn(salphen) structures, see: S. J. Wezenberg, E. C. Escudero-Adán, J. BenetBuchholz, A. W. Kleij, Chem. Eur. J. 2009, 15, 5695-5700.
38. a) A. L. Singer, D. A. Atwood, Inorg. Chim. Acta 1998, 277, 157-162.
39. b) A. W Kleij, M. Kuil, M. Lutz, D. M. Tooke, A. L. Spek, P. C. J. Kamer, P. W N M. Van Leeuwen, J. N. H. Reek, Inorg. Chim. Acta 2006, 359, 1807-1814.
40. c) C. T. L. Ma, M. J. MacLachlan, Angew. Chem. Int. Ed. 2005, 44, 4178-4182.
41. [6b]
42. 3.
43. 2O and the O-ligated 1-bmpy. We believe that this cocrystallization is caused by the hydrogen-bonding properties of the water ligand to adjacent Zn(salphen) complexes that consequently offers a better packing arrangement. For a related example, see
44. A. W. Kleij, D.M. Tooke, M. Kuil, M. Lutz, A. L. Spek, J. N. H. Reek, Chem. Eur. J. 2005, 11, 4743-4750.
45. E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Inorg. Chem. 2007, 46, 7265-7267.
46. M.-A. Muñoz-Hernández, T. S. Keizer, S. Parkin, B. Patrick, D. A. Atwood, Organometallics 2000, 19, 4416-4421.
47. E. C. Escudero-Adán, J. Benet-Buchholz, A. W Kleij, Eur. J. Inorg. Chem. 2009, 3562-3567.
48. K.-H. Chang, C.-C. Huang, Y.-H. Liu, Y.-H. Hu, P.-T. Chou, Y.-C. Lin, Dalton Trans. 2004, 1731-1738.