Recyclable dirhodium catalysts embedded in nanoporous surface-functionalized organosilica hosts for carbenoid-mediated cyclopropanation reactions

ChemCatChem

Volumn 2, Issue 11, 2010, Pages 1461-1466

  Dikarev, Evgeny V ^a   Kumar, D Krishna ^a   Filatov, Alexander S ^a   Anan, Abhishek ^b   Xie, Youwei ^b   Asefa, Tewodros ^b,c,d   Petrukhina, Marina A ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b SYRACUSE UNIVERSITY   (United States)

^c RUTGERS UNIVERSITY   (United States)

^d The State University of New Jersey   (United States)

Author keywords

Cyclopropanation; Heterogeneous catalysis; Mesoporous materials; Rhodium; Supported catalysts

Indexed keywords

EID: 79957843155     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201000142     Document Type: Article

References (74)

1. Chiral Catalysts Immobilization and Recycling (Eds.: D.E. De Vos, I.F.J. Vankelecom, P.A. Jacobs), Wiley-VCH, Weinheim, Germany, 2000;
2. Recoverable Catalysts and Reagents (Guest Ed.: J.A. Gladysz), Chem. Rev. 2002, 102 (theme issue);
3. K. D. M. Harris, J. M. Thomas, ChemCatChem 2009, 1, 223.
4. F. R. Hartley, M. Eisen, T. Bernstein, J. Blum, H. Schuman, J. Mol. Catal. 1981, 43, 199;
5. J. M. Fraile, J. I. Garcia, J. A. Mayoral, Chem. Commun. 1996, 1319;
6. J. M. Fraile, J. I. Garcia, J. A. Mayoral, Chem. Rev. 2009, 109, 360.
7. R. V. Parish, D. Habidi, V. Mohanmadi, J. Organomet. Chem. 1989, 369, 17;
8. H. Brunner, E. Bieldmeier, J. Wiehl, J. Organomet. Chem. 1990, 384, 223;
9. J. M. Fraile, J. I. Garcia, C. I. Herrerias, J. A. Mayoral, E. Pires, Chem. Soc. Rev. 2009, 38, 695.
10. C. U. Pittman in Polymer-Supported Reactions in Organic Synthesis (Eds.: P. Hodge, D.C. Sherrington), Wiley, Chichester, 1980, Chap.5;
11. Y. I. Yermakov, B. N. Kuznetsov, V. A. Zakharov, Catalysis by Supported Complexes, Elsevier, Amsterdam, 1981;
12. Solid Supports and Catalysts in Organic Synthesis (Ed.: K. Smith), Ellis Horwood, Chichester, 1992;
13. V. A. Likholobov, B. L. Moroz in Handbook of Heterogeneous Catalysis (Eds.: G. Ertl, H. Knözinger, J. Weitkamp), Wiley-VCH, Weinheim, 1997;
14. D. C. Sherrington, Supported Catalyst Immobilization and Their Applications, Springer, New York, 2001.
15. M. P. Doyle, M. Y. Eismont, D. E. Bergbreiter, H. N. Gray, J. Org. Chem. 1992, 57, 6103;
16. M. I. Burguete, J. M. Fraile, E. G. Verdugo, S. V. Luis, J. A. Mayoral, Org. Lett. 2000, 2, 3905;
17. M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045;
18. M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893;
19. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, M. Pitillo, J. Org. Chem. 2001, 66, 2587;
20. S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. 2001, 113, 2587; Angew. Chem. Int. Ed. 2001, 40, 2519;
21. D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493;
22. J. M. Fraile, J. I. Garcia, J. A. Mayoral, Coord. Chem. Rev. 2008, 252, 624.
23. M. Elliott, A. W. Farnhem, N. F. James, P. H. Needham, A. Pulman, J. H. Stevenson, Nature 1973, 246, 169;
24. D. Arlt, M. Jautelat, R. Lantzsch, Angew. Chem. 1981, 93, 719; Angew. Chem. Int. Ed. Engl. 1981, 20, 703.
25. nded., Academic Press, New York, 1971, p.85;
26. D. S. Wulfman, B. W. Peace, R. S. McDaniel Jr., Tetrahedron 1976, 32, 1231;
27. S. Patai, The Chemistry of Diazonium and Diazo Groups, Wiley, New York, 1978, p.615;
28. H. N. C. Wong, M.-V. Hon, C. W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165;
29. T. Hudlcky, J. W. Reed in Comprehensive Organic Synthesis, Vol.5 (Ed.: B.M. Trost), Pergamum Press, UK, 1991, p.989.
30. M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911;
31. "Chiral Dirhodium(II) Catalysts and Their Applications" D. J. Timmons, M. P. Doyle, Multiple Bonds Between Metal Atoms (Eds.: F.A. Cotton, C.A. Murillo, R.A. Walton), 3rd ed., Springer, Heidelberg, 2005, p.591;
32. H. M. L. Davies, S. J. Hedley, Chem. Soc. Rev. 2007, 36, 1109;
33. J. Hansen, H. M. L. Davies, Coord. Chem. Rev. 2008, 252, 545;
34. H. M. L. Davies, J. R. Denton, Chem. Soc. Rev. 2009, 38, 3061;
35. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704.
36. M. P. Doyle, D. J. Timmons, J. S. Tumonis, H.-M. Gau, E. C. Blossey, Organometallics 2002, 21, 1747.
37. T. Nagashima, H. M. L. Davies, Org. Lett. 2002, 4, 1989;
38. H. M. L. Davies, A. M. Walji, Org. Lett. 2003, 5, 479;
39. H. M. L. Davies, A. M. Walji, T. Nagashima, J. Am. Chem. Soc. 2004, 126, 4271;
40. H. M. L. Davies, A. M. Walji, Org. Lett. 2005, 7, 2941.
41. H. M. Hulman, M. de Lang, I. W. C. E. Arends, U. Hanefeld, R. A. Sheldon, T. Maschmeyer, J. Catal. 2003, 217, 264.
42. M. P. Doyle, M. Yan, H.-M. Gau, E. C. Blossey, Org. Lett. 2003, 5, 561;
43. J. Lloret, F. Estevan, K. Bieger, C. Villanueva, M. A. Úbeda, Organometallics 2007, 26, 4145;
44. J. Lloret, M. Stern, F. Estevan, M. Sanaú, M. A. Úbeda, Organometallics 2008, 27, 850.
45. Y. Sevryugina, B. Weaver, J. Hansen, J. Thompson, H. M. L. Davies, M. A. Petrukhina, Organometallics 2008, 27, 1750;
46. J. Hansen, B. Li, E. V. Dikarev, J. Autschbach, H. M. L. Davies, J. Org. Chem. 2009, 74, 6564.
47. W. Whitnall, T. Asefa, G. A. Ozin, Adv. Funct. Mater. 2005, 15, 1696;
48. K. K. Sharma, T. Asefa, Angew. Chem. 2007, 119, 2937; Angew. Chem. Int. Ed. 2007, 46, 2879;
49. N. Garcia, E. Benito, J. Guzman, P. Tiemblo, J. Am. Chem. Soc. 2007, 129, 5052;
50. C. Zapilko, Y.-C. Liang, W. Nerdal, R. Anwander, Chem. Eur. J. 2007, 13, 3169;
51. A. Anan, K. K. Sharma, T. Asefa, J. Mol. Catal. A 2008, 288, 1;
52. K. K. Sharma, A. Anan, R. P. Buckley, W. Ouellette, T. Asefa, J. Am. Chem. Soc. 2008, 130, 218.
53. F. A. Cotton, E. V. Dikarev, M. A. Petrukhina, M. Schmitz, P. J. Stang, Inorg. Chem. 2002, 41, 2903;
54. E. V. Dikarev, V. V. Chernyshev, R. V. Shpanchenko, A. S. Filatov, M. A. Petrukhina, Dalton Trans. 2004, 4120;
55. E. V. Dikarev, B. Li, V. V. Chernyshev, R. V. Shpanchenko, M. A. Petrukhina, Chem. Commun. 2005, 3274.
56. E. Nakamura, N. Yoshikai, M. Yamanaka, J. Am. Chem. Soc. 2002, 124, 7181;
57. M. C. Pirrung, H. Liu, A. T. Morehead, J. Am. Chem. Soc. 2002, 124, 1014.
58. F. A. Cotton, E. V. Dikarev, X. Feng, Inorg. Chim. Acta 1995, 237, 19;
59. F. A. Cotton, E. V. Dikarev, M. A. Petrukhina, J. Am. Chem. Soc. 2001, 123, 11655;
60. E. V. Dikarev, K. W. Andreini, M. A. Petrukhina, Inorg. Chem. 2004, 43, 329;
61. A. S. Filatov, A. Yu. Rogachev, M. A. Petrukhina, Cryst. Growth Des. 2006, 6, 1479;
62. A. Yu. Rogachev, M. A. Petrukhina, J. Phys. Chem. A 2009, 113, 5743.
63. P. Cmoch, J. Jaźwiński, J. Mol. Struct. 2009, 919, 348.
64. W. A. J. Starmans, L. Thijs, B. Zwanenburg, Tetrahedron 1998, 54, 629.
65. H. M. L. Davies, L. Rusiniak, Tetrahedron Lett. 1998, 39, 8811.
66. M. J. Alcon, A. Corma, M. Iglesias, F. Sanchez, J. Mol. Catal. A 1999, 144, 337;
67. A. Prieto, M. R. Fructos, M. M. Diraz-Requejo, P. J. Perez, P. Perez-Galan, N. Delpont, A. M. Echavarren, Tetrahedron 2009, 65, 1790.
68. A. J. Anciaux, A. J. Hubert, A. F. Noels, N. Petiniot, P. Teyssie, J. Org. Chem. 1980, 45, 695;
69. M. P. Doyle, J. H. Griffin, V. Bagheri, R. L. Dorow, Organometallics 1984, 3, 53;
70. M. P. Doyle, V. Bagheri, T. J. Wandless, N. K. Harn, D. A. Brinker, C. T. Eagle, K.-L. Loh, J. Am. Chem. Soc. 1990, 112, 1906.
71. E. de Smit, I. Swart, J. F. Creemer, G. H. Hoveling, M. K. Gilles, T. Tyliszczak, P. J. Kooyman, H. W. Zandbergen, C. Morin, B. M. Weckhuysen, F. M. F. Groot, Nature 2008, 456, 222.
72. F. A. Cotton, T. R. Felthouse, Inorg. Chem. 1980, 19, 2347;
73. F. A. Cotton, T. R. Felthouse, Inorg. Chem. 1981, 20, 600.
74. D. Zhao, J. Feng, Q. Huo, N. Melosh, G. H. Fredrickson, B. F. Chmelka, G. D. Stucky, Science 1998, 279, 548.