N-tetradentate spanamine derivatives and their MnII-complexes as catalysts for epoxidation of alkenes

European Journal of Inorganic Chemistry

Volumn , Issue 7, 2013, Pages 1213-1224

  Rich, Jordi ^a   Rodríguez, Montserrat ^a   Romero, Isabel ^a   Fontrodona, Xavier ^a   Van Leeuwen, Piet W N M ^b   Freixa, Zoraida ^b,c   Sala, Xavier ^d   Poater, Albert ^a,e   Solà, Miquel ^a  

^a Institut de Quimica Computacional   (Spain)

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

^c UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^d UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^e UNIVERSITY OF GIRONA   (Spain)

Author keywords

Epoxidation; Heterogeneous catalysis; Manganese; N ligands; Spiro compounds

Indexed keywords

CATALYSTS; LIGANDS; MANGANESE COMPOUNDS; STYRENE; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

COMPUTATIONAL CALCULATIONS; EPOXIDATION OF ALKENES; METHYLSTYRENE; N LIGANDS; N-LIGANDS; SPIRO-COMPOUNDS; STEREOSPECIFICITY; SYNTHESISED; TETRADENTATE; ]+ CATALYST;

CATALYSIS;

EID: 84874232745     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201201154     Document Type: Article

References (69)

1. R. A. Sheldon, J. K. Kochi, Metal Catalyzed Oxidation of Organic Compounds, Academic Press, New York, 1981.
2. A. Robert, B. Meunier, Biomimetic Oxidations Catalyzed by Transition Metal Complexes (Ed.:, B. Meunier), Imperial College Press, London, 2000, chapter 12.
3. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3070.
4. Z. Freixa, P. W. N. M. van Leeuwen, Coord. Chem. Rev. 2008, 252, 1755-1786.
5. M.-N. Birkholz, Z. Freixa, P. W. N. M. van Leeuwen, Chem. Soc. Rev. 2009, 38, 1099-1118.
6. M. Gõmez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769-835.
7. G. C. Hargaden, P. J. Guiry, Chem. Rev. 2009, 109, 2505-2550.
8. Y. L. Bennani, S. Hanessian, Chem. Rev. 1997, 97, 3161-3196.
9. J.-C. Kizirian, Chem. Rev. 2008, 108, 140-205.
10. H. A. McManus, P. J. Guiry, Chem. Rev. 2004, 104, 4151-4202.
11. R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345-350.
12. M. J. Burk, Acc. Chem. Res. 2000, 33, 363-372.
13. A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345.
14. A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
15. J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335.
16. G. Desimoni, G. Faita, K. A. Jorgensen, Chem. Rev. 2006, 106, 3561-3651.
17. M. Palucki, M. S. Finney, P. J. Pospisil, M. L. Güler, T. Ishida, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 948-954.
18. T. Katsuky, Adv. Synth. Catal. 2002, 344, 131-147.
19. P. G. Cozzi, Chem. Soc. Rev. 2004, 33, 410-421.
20. Z. Freixa, M. S. Beentjes, G. D. Batema, C. B. Dieleman, G. P. F. van Strijdonck, J. N. H. Reek, P. C. J. Kamer, J. Fraanje, K. Goubitz, P. W. N. M. van Leeuwen, Angew. Chem. 2003, 115, 1322-1325; Angew. Chem. Int. Ed. 2003, 42, 1284 -1287.
21. Z. Freixa, P. C. J. Kamer, M. Lutz, A. L. Spek, P. W. N. M. van Leeuwen, Angew. Chem. 2005, 117, 4459-4462; Angew. Chem. Int. Ed. 2005, 44, 4385 -4388.
22. C. Jiménez-Rodríguez, F. X. Roca, C. Bo, J. Benet-Buchholz, E. C. Escudero-Adán, Z. Freixa, P. W. N. M. van Leeuwen, Dalton Trans. 2006, 268-278.
23. X. Sala, E. J. García Suárez, Z. Freixa, J. Benet-Buchholz, P. W. N. M. van Leeuwen, Eur. J. Org. Chem. 2008, 6197-6205.
24. O. Jacquet, N. D. Clément, Z. Freixa, A. Ruiz, C. Claver, P. W. N. M. van Leeuwen, Tetrahedron: Asymmetry 2011, 22, 1490-1498.
25. J. Li, G. Chen, Z. Wang, R. Zhang, X. Zhang, K. Ding, Chem. Sci. 2011, 2, 1141-1144.
26. X. Wang, Z. Han, Z. Wang, K. Ding, Angew. Chem. Int. Ed. 2012, 51, 936-940.
27. F. Fache, E. Schulz, L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231.
28. M. Hechavarría Fonseca, B. König, Adv. Synth. Catal. 2003, 345, 1173-1185.
29. C. A. Caputo, N. D. Jones, Dalton Trans. 2007, 4627-4640.
30. A. von Zelewsky, O. Mamula, J. Chem. Soc., Dalton Trans. 2000, 219-231.
31. G. Chelucci, R. P. Thummel, Chem. Rev. 2002, 102, 3129-3170.
32. J. Rich, M. Rodríguez, I. Romero, L. Vaquer, X. Sala, A. Llobet, M. Corbella, M.-N. Collomb, X. Fontrodona, Dalton Trans. 2009, 8117-8126.
33. B. Meunier, Chem. Rev. 1992, 92, 1411-1456.
34. L. Gõmez, I. Garcia-Bosch, A. Company, X. Sala, X. Fontrodona, X. Ribas, M. Costas, Dalton Trans. 2007, 5539-5545.
35. O. Jacquet, N. D. Clement, O. Martínez, M. Serrano, C. Claver, P. W. N. M. van Leeuwen, unpublished work.
36. A. L. Sauers, D. M. Ho, S. Bernhard, J. Org. Chem. 2004, 69, 8910-8915.
37. X. Sala, A. M. Rodríguez, M. Rodríguez, I. Romero, T. Parella, A. von Zelewsky, A. Llobet, J. Benet-Buchholz, J. Org. Chem. 2006, 71, 9283-9290.
38. C. Vedder, F. Schaper, H. H. Brintzinger, M. Kettunen, S. Babik, G. Fink, Eur. J. Inorg. Chem. 2005, 1071-1080.
39. P. A. Goodson, J. Glerop, D. J. Hodgson, K. Michelsen, H. Weihe, Inorg. Chem. 1991, 30, 4909-4914.
40. J. Rich, M. Rodríguez, I. Romero, F. Molton, C. Duboc, M. N. Collomb, manuscript submitted.
41. A. Murphy, A. Pace, T. D. P. Stack, Org. Lett. 2004, 6, 3119-3122.
42. K. Campbell, M. R. Lashley, J. K. Wyatt, M. H. Nantz, R. D. Britt, J. Am. Chem. Soc. 2001, 123, 5710-5719.
43. B. S. Lane, M. Vogt, V. J. DeRose, K. Burgess, J. Am. Chem. Soc. 2002, 124, 11946-11954.
44. A. Murphy, G. A. Dubois, T. D. P. Stack, J. Am. Chem. Soc. 2003, 125, 5250-5251.
45. X. Sala, E. Plantalech, I. Romero, M. Rodríguez, A. Llobet, A. Poater, M. Duran, M. Solà, S. Jansat, M. Gõmez, T. Parella, H. Stoeckli-Evans, J. Benet-Buchholz, Chem. Eur. J. 2006, 12, 2798-2807.
46. J. Mola, M. Rodríguez, I. Romero, A. Llobet, T. Parella, A. Poater, M. Duran, M. Solà, J. Benet-Buchholz, Inorg. Chem. 2006, 45, 10520-10529.
47. A. Poater, L. Cavallo, Inorg. Chem. 2009, 48, 4062-4066.
48. A. Poater, X. Ribas, A. Llobet, L. Cavallo, M. Solà, J. Am. Chem. Soc. 2008, 130, 17710-17717.
49. J. Benet-Buchholz, P. Comba, A. Llobet, S. Roeser, P. Vadivelu, H. Wadepohl, S. Wiesner, Dalton Trans. 2009, 5910-5923.
50. M. Torrent, L. Deng, M. Duran, M. Solà, T. Ziegler, Can. J. Chem. 1999, 77, 1476-1491.
51. Y. Inada, Y. Nakano, M. Inamo, S. Funashashi, Inorg. Chem. 2000, 39, 4793-4801.
52. SMART, version 5.631, Bruker Advanced X-ray Solutions, 1997-2002.
53. SAINT +, Bruker Advanced X-ray Solutions, version 6.36A, 2001.
54. G. M. Sheldrick, Empirical Absorption Correction Program, University of Göttingen, Germany, 1996. SADABS, version 2.10, Bruker Advanced X-ray Solutions, 2001.
55. G. M. Sheldrick, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997. SHELXTL, version 6.14, Bruker Advanced X-ray Solutions, 2000-2003.
56. Data collection with APEX II versions 1.0-22, 2009.1-0 and 2009.1-02. Bruker AXS Inc., Madison, Wisconsin, USA, 2007.
57. Data reduction with SAINT versions 2.10 (2003), /.60A and 7.60A, Bruker AXS Inc., Madison, Wisconsin, USA, 2007.
58. TWINABS, version 2008/4, Bruker AXS:, R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-38.
59. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122. XTL, versions 6.12 and 6.14.
60. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision A.1, Gaussian, Inc., Wallingford CT, 2009.
61. A. Becke, Phys. Rev. A 1988, 38, 3098-3100.
62. J. P. Perdew, Phys. Rev. B 1986, 33, 8822-8824.
63. J. P. Perdew, Phys. Rev. B 1986, 34, 7406-7406.
64. A. Schaefer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577.
65. U. Haeusermann, M. Dolg, H. Stoll, H. Preuss, Mol. Phys. 1993, 78, 1211-1224.
66. W. Kuechle, M. Dolg, H. Stoll, H. Preuss, J. Chem. Phys. 1994, 100, 7535-7542.
67. T. Leininger, A. Nicklass, H. Stoll, M. Dolg, P. Schwerdtfeger, J. Chem. Phys. 1996, 105, 1052-1059.
68. V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995-2001.
69. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094.