Nonsymmetrical salen ligands and their complexes: Synthesis and applications

European Journal of Inorganic Chemistry

Volumn , Issue 2, 2009, Pages 193-205

  Kleij, Arjan W ^a,b  

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

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

Author keywords

Asymmetric catalysis; Ligand design; N,O ligands; Nonsymmetrical ligands

Indexed keywords

CATALYSIS; CATALYSTS; CHELATION; STEEL BEAMS AND GIRDERS; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; HOMOGENEOUS CATALYSIS; HOMOGENEOUS MATERIALS; LIGAND DESIGN; MATERIAL CHEMISTRY; N,O LIGAND; NONSYMMETRICAL LIGAND; O LIGANDS; SALEN LIGANDS; ]+ CATALYST;

LIGANDS;

EID: 58249130323     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200800936     Document Type: Short Survey

References (117)

1. The term "salen" here will be used throughout this review as a general name for this kind of ligand. Where needed, the exact nature of the ligand will be structurally detailed. For selected reviews on this subject see: a) L. Canali, D. C. Sherrington, Chem. Soc. Rev. 1999, 28, 85-93;
2. b) J. F. Larrow, E. N. Jacobsen, Top. Organomet. Chem. 2004, 6, 123-152;
3. c) T. Katsuki, Adv. Synth. Catal. 2002, 344, 131-147;
4. d) P. G. Cozzi, Chem. Soc. Rev. 2004, 33, 410-421;
5. e) S. J. Wezenberg, A. W. Kleij, Angew. Chem. Int. Ed. 2008, 47, 2354-2364;
6. f) E. M. McGarrigle, D. G. Gilheany, Chem. Rev. 2005, 105, 1563-1602;
7. g) A. W. Kleij, Chem. Eur. J. 2008, early view (DOI: 10.1002/chem.200801149);
8. h) D. A. Atwood, M. J. Harvey, Chem. Rev. 2001; 101, 37-52;
9. i) D. J. Darensbourg, Chem. Rev. 2007, 107, 2388-2410;
10. j) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
11. k) E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431;
12. l) A. Dalla Cort, C. Pasquini, L. Schiaffino, Supramol. Chem. 2007, 19, 79-87;
13. m) T. Katsuki, Chem. Soc. Rev. 2004, 33, 437-444;
14. n) N. Madhavan, C. W. Jones, M. Weck, Acc. Chem. Res. 2008, 41, 1153-1165.
15. a) W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801-2803;
16. b) R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki, Tetrahedron Lett. 1990, 31, 7345-7348.
17. See for instance: a) J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939-1942;
18. b) M. Palucki, N. S. Finney, P. J. Pospisil, M. L. Güler, T. Ishida, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 948-954;
19. For recent theoretical studies devoted to electronic effects in these systems: c) L. Cavallo, H. Jacobsen, J. Org. Chem. 2003, 68, 6202-6207.
20. For a few examples of polymer-supported (symmetrical) metallosalen catalyst see: a) F. Minutolo, D. Pini, P. Salvadori, Tetrahedron: Asymmetry 1996, 7, 2293-2302;
21. b) F. Minutolo, D. Pini, P. Salvadori, Tetrahedron Lett. 1996, 37, 3375-3378.
22. Please refer to section 2.
23. For examples of dendritic catalysts with metallosalen fragments: a) R. Breinbauer, E. N. Jacobsen, Angew. Chem. Int. Ed. 2000, 39, 3604-3607;
24. b) H. Sellner, J. K. Karjalainen, D. Seebach, Chem. Eur. J. 2001, 7, 2873-2887.
25. Please refer to section 2.
26. a) G.-J. Kim, J.-H. Shin, Catal. Lett. 1999, 63, 83-90;
27. b) M. F. Renehan, H.-J. Schanz, E. M. McGarrigle, C. T. Dalton, A. M. Daly, D. G. Gilheany, J. Mol. Catal. A 2005, 231, 205-220.
28. R. Atkins, G. Brewer, E. Kokot, G. M. Mockler, E. Sinn, Inorg. Chem. 1985, 24, 127-134.
29. For similar approaches through mono- and/or diketimine intermediates see: a) X.-D. Du, X.-D. Yu, J. Mol. Catal. A 1997, 126, 109-133;
30. b) D. M. Boghaei, S. Mohebi, Tetrahedron 2002, 58, 5357-5366;
31. c) A. Böttcher, H. Elias, B. Eisenmann, E. Hilms, A. Huber, R. Kniep, C. Röhr, M. Zehnder, M. Neuburger, J. Springborg, Z. Naturforsch., Teil B 1994, 49, 1089-1100;
32. d) A. Huber, L. Müller, H. Elias, R. Klement, M. Valko, Eur. J. Inorg. Chem. 2005, 1459-1467;
33. e) R. I. Kureshy, N. H. Khan, S. H. R. Abdi, A. K. Bhatt, J. Mol. Catal. A 1996, 110, 33-40;
34. f) R. I. Kureshy, N. H. Khan, S. H. R. Abdi, P. Iyer, A. K. Bhatt, J. Mol. Catal. A 1997, 120, 101-108;
35. g) R. I. Kureshy, N. H. Khan, S. H. R. Abdi, P. Iyer, S. T. Patel, Polyhedron 1996, 110, 33-40.
36. A. Yeori, S. Gendler, S. Groysman, I. Goldberg, M. Kol, Inorg. Chem. Commun. 2004, 7, 280-282.
37. a) R. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10780-10781.
38. IIIsalen complexes useful in cooperative catalysis see: b) C. Mazet, E. N. Jacobsen, Angew. Chem. Int. Ed. 2008, 47, 1762-1765.
39. a) D. Allen Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154.
40. For another interesting example see: b) U. K. Anyanwu, D. Venkataraman, Tetrahedron Lett. 2003, 44, 6445-6448.
41. III-salen complexes with two pending hydroxy groups in the 5 and 5′ position of the phenyl side groups have been used to construct symmetrical, cyclic oligosalen catalysts useful in cooperative campaigns. See: a) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688;
42. b) J. M. Ready, E. N. Jacobsen, Angew. Chem. Int. Ed. 2002, 41, 1374-1377;
43. c) D. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633-3638.
44. a) L. Canali, E. Cowan, H. Deleuze, C. L. Gibson, D. C. Sherrington, Chem. Commun. 1998, 2561-2562.
45. For other examples using a direct approach for nonsymmetrical salen derivatives attached to polymeric and other supports see: b) C. Baleizão, H. García, Chem. Rev. 2006, 106, 3987-4043 and references cited therein;
46. c) A. Corma, H. Garcia, Adv. Synth. Catal. 2006, 348, 1391-1412;
47. d) M. Alvaro, C. Baleizão, E. Carbonell, M. El Ghoul, H. García, B. Gigante, Tetrahedron 2005, 61, 12131-12139;
48. e) M. D. Angelino, P. E. Laibinis, Macromolecules 1998, 31, 7581-7587;
49. f) D. C. Sherrington, Catal. Today 2000, 57, 87-104 and references cited therein;
50. g) M. Nielsen, K. V. Gothelf, J. Chem. Soc. Perkin Trans. 1 2004, 2440-2444.
51. B. M. Rossbach, K. Leopold, R. Weberskirch, Angew. Chem. Int. Ed. 2006, 45, 1309-1312.
52. P. Goyal, X. Zheng, M. Weck, Adv. Synth. Catal. 2008, 350, 1816-1822.
53. [10a];
54. b) W. Solodenko, G. Jas, U. Kunz, A. Kirschning, Synthesis 2007, 583-589.
55. M. Holbach, X. Zheng, C. Burd, C. W. Jones, M. Weck, J. Org. Chem. 2006, 71, 2903-2906.
56. a) R. I. Kureshy, N. H. Khan, S. H. R. Abdi, S. Singh, I. Ahmad, R. V. Jasra, A. P. Vyas, J. Catal. 2004, 224, 229-235;
57. b) R. I. Kureshy, N. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, J. Mol. Catal. A 2002, 179, 73-77;
58. c) R. I. Kureshy, N. H. Khan, S. H. R. Abdi, S. T. Patel, R. V. Jasra, Tetrahedron: Asymmetry 2001, 12, 433-437.
59. a) A. M. Daly, C. T. Dalton, M. F. Renehan, D. G. Gilheany, Tetrahedron Lett. 1999, 40, 3617-3620;
60. b) see also ref.[8b] for a full account.
61. Although an earlier report exists on the high yield synthesis of nonsymmetrical salen derivatives, several groups have reported problems with the reproducibility of these results: J. Lopez, S. Liang, X. R. Bu, Tetrahedron Lett. 1998, 39, 4199-4202.
62. E. J. Campbell, S. T. Nguyen, Tetrahedron Lett. 2001, 42, 1221-1224.
63. X. Zheng, C. W. Jones, M. Weck, J. Am. Chem. Soc. 2007, 129, 1105-1112.
64. J. A. Love, J. P. Morgan, T. M. Trnka, R. H. Grubbs, Angew. Chem. Int. Ed. 2002, 41, 4035-4037.
65. [6b]
66. X. Zheng, C. W. Jones, M. Weck, Chem. Eur. J. 2006, 12, 576-583.
67. M. Holbach, M. Weck, J. Org. Chem. 2006, 71, 1825-1836.
68. For some representative examples of 1,4-conjugate additions see: a) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 5315-5316;
69. b) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11204-11205;
70. c) M. Gandelman, E. N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 2393-2397;
71. d) M. Bandini, M. Fagioli, M. Garavelli, A. Melloni, V. Trigari, A. Umani-Ronchi, J. Org. Chem. 2004, 69, 7511-7518.
72. N. Madhavan, M. Weck, Adv. Synt. Catal. 2008, 350, 419-425.
73. M.-A. Muñoz-Hernández, T. S. Keizer, S. Parkin, B. Patrick, D. A. Atwood, Organometallics 2000, 19, 4416-4421.
74. A. W. Kleij, D. M. Tooke, A. L. Spek, J. N. H. Reek, Eur. J. Inorg. Chem. 2005, 4626-4634.
75. II-salpyr compounds: a) A. W. Kleij, M. Kuil, D. M. Tooke, A. L. Spek, J. N. H. Reek, Inorg. Chem. 2007, 46, 5829-5831;
76. b) G. Li, W. Yu, J. Ni, T. Liu, Y. Liu, E. Sheng, Y. Cui, Angew. Chem. Int. Ed. 2008, 47, 1245-1249;
77. c) K.-H. Chang, C.-C. Huang, Y.-H. Liu, Y.-H. Hu, P.-T. Chou, Y.-C. Lin, Dalton Trans. 2007, 1731-1738;
78. d) K.-L. Kuo, C.-C. Huang, Y.-C. Lin, Dalton Trans. 2008, 3889-3898.
79. a) S. Curreli, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, J. Org. Chem. 2007, 72, 7018-7021;
80. b) S. Curreli, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Eur. J. Inorg. Chem. 2008, 2863-2873.
81. A. W. Kleij, D. M. Tooke, M. Kuil, M. Lutz, A. L. Spek, J. N. H. Reek, Chem. Eur. J. 2005, 11, 4743-4750.
82. A. W. Kleij, M. Lutz, A. L. Spek, P. W. N. M. van Leeuwen, J. N. H. Reek, Chem. Commun. 2005, 3661-3663.
83. 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 2005, 359, 1807-1814.
84. 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.
85. L. Rigamonti, F. Demartin, A. Forni, S. Righetto, A. Pasini, Inorg. Chem. 2006, 45, 10976-10989.
86. For further experimental details see also: J.-P. Costes, F. Dahan, M. B. Fernandez Fernandez, M. I. Fernandez Garcia, A. M. Garcia Deibe, J. Sanmartin, Inorg. Chim. Acta 1998, 274, 73-81.
87. C. Benelli, A. Caneschi, D. Gatteschi, O. Guillou, L. Pardi, Inorg. Chem. 1990, 29, 1750-1755.
88. R.-J. Tao, C.-Z. Mei, S.-Q. Zang, Q.-L. Wang, J.-Y. Niu, D.-Z. Liao, Inorg. Chim. Acta 2004, 357, 1985-1990.
89. A. Dalla Cort, L. Mandolini, G. Palmieri, C. Pasquini, L. Schiaffino, Chem. Commun. 2003, 2178-2179. See also ref.[1l] for a review on uranyl-salen chemistry.
90. M. Cametti, M. Nissinen, A. Dalla Cort, L. Mandolini, K. Rissanen, J. Am. Chem. Soc. 2005, 127, 3831-3837.
91. V. van Axel Castelli, A. Dalla Cort, L. Mandolini, V. Pinto, D. N. Reinhoudt, F. Ribaudo, C. Sanna, L. Schiaffino, B. H. M. Snellink-Ruël, Supramol. Chem. 2002, 14, 211-219.
92. A. Dalla Cort, J. I. Miranda Murua, C. Pasquini, M. Pons, L. Schiaffino, Chem. Eur. J. 2004, 10, 3301-3307.
93. A. Dalla Cort, L. Mandolini, L. Schiaffino, Chem. Commun. 2005, 3867-3869.
94. V. van Axel Castelli, A. Dalla Cort, L. Mandolini, V. Pinto, L. Schiaffino, J. Org. Chem. 2007, 72, 5383-5386.
95. K. Ambroziak, M. Szypa, Tetrahedron Lett. 2007, 48, 3331-3335.
96. T. Glaser, M. Heidemeier, T. Lügger, Dalton Trans. 2003, 2381-2383.
97. See for the use of (multimetallic)salen complexes as adsorption materials and sensors: a) E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Inorg. Chem. 2008, 47, 4256-4263;
98. b) S. J. Wezenberg, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Org. Lett. 2008, 10, 3311-3314;
99. c) A. Dalla-Cort, L. Mandolini, C. Pasquini, K. Rissanen, L. Russo, L. Schiaffino, New J. Chem. 2007, 31, 1633-1638;
100. d) M. E. Germain, T. R. Vargo, P. G. Khalifah, M. J. Knapp, Inorg. Chem. 2007, 46, 4422-4429;
101. e) M. E. Germain, M. J. Knapp, J. Am. Chem. Soc. 2008, 130, 5422-5423.
102. a) N. E. Borisova, M. D. Reshetova, Y. A. Ustynyuk, Chem. Rev. 2007, 107, 46-79;
103. b) P. A. Vigato, S. Tamburini, L. Bertolo, Chem. Rev. 2007, 107, 1311-1492.
104. For a recent example: P. D. Frischmann, A. J. Gallant, J. H. Chong, M. MacLachlan, Inorg. Chem. 2008, 47, 101-112.
105. P. D. Frischmann, J. Jiang, J. K.-H. Hui, J. J. Grzybowski, M. J. MacLachlan, Org. Lett. 2008, 10, 1255-1258.
106. S. Akine, T. Taniguchi, T. Nabeshima, J. Am. Chem. Soc. 2006, 128, 15765-15774.
107. Y.-M. Lin, J. Boucau, Z. Li, V. Casarotto, J. Lin, A. N. Nguyen, J. Ehrmantraut, Org. Lett. 2007, 9, 567-570.
108. a) M. Cametti, A. Dalla Cort, M. Colapietro, G. Portalone, L. Russo, K. Rissanen, Inorg. Chem. 2007, 46, 9057-9059;
109. b) For another similar example: Y. Wang, S. Parkin, D. A. Atwood, Inorg. Chem. 2002, 41, 558-565.
110. J. A. Miller, B. A. Gross, M. A. Zhuravel, W. Jin, S. T. Nguyen, Angew. Chem. Int. Ed. 2005, 44, 3885-3889.
111. a) G. H. Clever, K. Polborn, T. Carell, Angew. Chem. Int. Ed. 2005, 44, 7204-7208;
112. b) G. H. Clever, Y. Söltl, H. Burks, W. Spahl, T. Carell, Chem. Eur. J. 2006, 12, 8708-8718.
113. For some other salen-based DNA templated systems see: a) J. L. Czlapinski, T. L. Sheppard, J. Am. Chem. Soc. 2001, 123, 8618-8619;
114. b) J. L. Czlapinski, T. L. Sheppard, ChemBioChem 2004, 5, 127-129.
115. K. Tanaka, G. H. Clever, Y. Takezawa, Y. Yamada, C. Kaul, M. Shionoya, T. Carell, Nat. Nanotechnol. 2006, 1, 190-194.
116. For an example see: S.-S. Sun, C. L. Stern, S. T. Nguyen, J. T. Hupp, J. Am. Chem. Soc. 2004, 126, 6314-6326.
117. S. J. Wezenberg, E. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Inorg. Chem. 2008, 47, 2925-2927.