Synthesis, immobilization, MAS and HR-MAS NMR of a new chelate phosphine linker system, and catalysis by rhodium adducts thereof

Advanced Synthesis and Catalysis

Volumn 353, Issue 2-3, 2011, Pages 443-460

  Guenther, J ^a   Reibenspies, J ^a   Blumel J ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

chelate phosphines; immobilization; immobilized catalysts; phosphonium salts; rhodium complexes; rhodium nanoparticles

Indexed keywords

EID: 79951833545     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000585     Document Type: Article

References (87)

1. K. C. Nicolaou, R. Hanko, W. Hartwig, (Eds.), Handbook of Combinatorial Chemistry, Wiley-VCH, Weinheim, Germany, 2002, Vols. 1 and 2
2. W. Bannworth, E. Felder, (Eds.), Combinatorial Chemistry, Wiley-VCH, Weinheim, Germany, 2000
3. J. A. Gladysz, (Ed.), Recoverable Catalysts and Reagents, Special Issue of Chem. Rev. 2002, 102
4. J. Blümel, Coord. Chem. Rev. 2008, 252, 2410-2423
5. F. R. Hartley, Supported Metal Complexes, D. Reidel Publ. Co., Dordrecht, The Netherlands, 1985
6. D. E. DeVos, I. F. J. Vankelecom, P. A. Jacobs, (Eds.), Chiral Catalyst Immobilization and Recycling, Wiley-VCH, Weinheim, 2000
7. G. Rothenberg, Catalysis: Concepts and Green Applications, Wiley-VCH, Weinheim, 2008.
8. E. F. Vansant, P. VanDer Voort, K. C. Vrancken, Characterization and Chemical Modification of the Silica Surface, Elsevier, Amsterdam, 1995
9. R. P. W. Scott, Silica Gel and Bonded Phases, John Wiley and Sons, New York, 1993.
10. S. Reinhard, P. Soba, F. Rominger, J. Blümel, Adv. Synth. Catal. 2003, 345, 589-602
11. K. D. Behringer, J. Blümel, Chem. Commun. 1996, 653-654
12. S. Reinhard, K. D. Behringer, J. Blümel, New J. Chem. 2003, 27, 776-778.
13. C. Merckle, J. Blümel, Adv. Synth. Catal. 2003, 345, 584-588
14. C. Merckle, J. Blümel, Top. Catal. 2005, 34, 5-15
15. C. Merckle, S. Haubrich, J. Blümel, J. Organomet. Chem. 2001, 627, 44-54.
16. Y. Yang, B. Beele, J. Blümel, J. Am. Chem. Soc. 2008, 130, 3771-3773
17. B. Beele, J. Guenther, M. Perera, M. Stach, T. Oeser, J. Blümel, New J. Chem. 2010, 34, 2729-2731.
18. N. Lewanzik, T. Oeser, J. Blümel, J. A. Gladysz, J. Mol. Catal. A: Chemical 2006, 254, 20-28.
19. T. Posset, F. Rominger, J. Blümel, Chem. Mater. 2005, 17, 586-595
20. F. Piestert, R. Fetouaki, M. Bogza, T. Oeser, J. Blümel, Chem. Commun. 2005, 1481-1483.
21. M. Bogza, T. Oeser, J. Blümel, J. Organomet. Chem. 2005, 690, 3383-3389.
22. R. Fetouaki, A. Seifert, M. Bogza, T. Oeser, J. Blümel, Inorg. Chim. Acta 2006, 359, 4865-4873.
23. T. M. Duncan, A Compilation of Chemical Shift Anisotropies, Farragut Press, Chicago, IL, 1990
24. C. A. Fyfe, Solid-State NMR for Chemists, C.F.C. Press, Guelph, Canada, 1983
25. M. J. Duer, Introduction to Solid-State NMR Spectroscopy, Blackwell Publishing, Oxford, 2004
26. S. Reinhard, J. Blümel, Magn. Reson. Chem. 2003, 41, 406-416.
27. S. Brenna, T. Posset, J. Furrer, J. Blümel, Chem. Eur. J. 2006, 12, 2880-2888
28. T. Posset, J. Blümel, J. Am. Chem. Soc. 2006, 128, 8394-8395.
29. P. W. Clark, J. L. S. Curtis, P. E. Garrou, G. E. Hartwell, Can. J. Chem. 1974, 52, 1714-1720
30. P. W. Clark, G. E. Hartwell, Inorg. Chem. 1970, 9, 1948-1951
31. P. W. Clark, A. J. Jones, J. Organomet. Chem. 1976, 122, C 41 -C 48.
32. T. Hirai, L.-B. Han, Org. Lett. 2007, 9, 53-55.
33. T. Shima, F. Hampel, J. A. Gladysz, Angew. Chem. 2004, 116, 5653-5656
34. Angew. Chem. Int. Ed. 2004, 43, 5537-5540
35. A. J. Nawara-Hultzsch, K. Skopek, T. Shima, M. Barbasiewicz, G. D. Hess, D. Skaper, J. A. Gladysz, Z. Naturforsch. 2010, 65b, 414-424.
36. G. Fraenkel, W. R. Winchester, P. G. Williard, Organometallics 1989, 8, 2308-2311.
37. J. Cámpora, C. M. Maya, I. Matas, B. Claasen, P. Palma, E. ßlvarez, Inorg. Chim. Acta 2006, 359, 3191-3196.
38. -1. Further crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 782510. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
39. M. Baacke, O. Stelzer, V. Wray, Chem. Ber. 1980, 113, 1356-1369.
40. G. Tsiavaliaris, S. Haubrich, C. Merckle, J. Blümel, Synlett 2001, 391-393.
41. 2 indicated the possibility of disorder. Given the poor quality of the data, no further attempts were made to model the disorder. Some of the weak residual electron densities could not be deciphered into any realistic solvent. At this stage, the data was squeezed using PLATON which indicated the presence of 141 electrons per unit cell: corresponding well with four pentane molecules [=140 electrons]). Further crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 782509. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
42. S. Herold, A. Mezzetti, L. M. Venanzi, A. Albinati, F. Lianza, T. Gerfin, V. Gramlich, Inorg. Chim. Acta 1995, 235, 215-231
43. F. Bachechi, J. Ott, L. Venanzi, Acta Crystallogr. 1989, C45, 724-728.
44. B. E. Hauger, J. C. Huffman, K. G. Caulton, Organometallics 1996, 15, 1856-1864.
45. J. Scherer, G. Huttner, O. Walter, B. C. Janssen, L. Zsolnai, Chem. Ber. 1996, 129, 1603-1615
46. C. Bianchini, C. A. Ghilardi, A. Meli, S. Midollini, A. Orlandini, Inorg. Chem. 1985, 24, 924-931
47. A. A. Barney, A. F. Heyduk, D. G. Nocera, Chem. Commun. 1999, 2379-2380
48. J. C. Peters, J. D. Feldman, T. D. Tilley, J. Am. Chem. Soc. 1999, 121, 9871-9872
49. S. Jiménez, J. A. Lõpez, M. A. Ciriano, C. Tejel, A. Martínez, R. A. Sánchez-Delgado, Organometallics 2009, 28, 3193-3202.
50. C. Merckle, J. Blümel, Chem. Mater. 2001, 13, 3617-3623
51. J. Blümel, J. Am. Chem. Soc. 1995, 117, 2112-2113
52. K. D. Behringer, J. Blümel, J. Liq. Chromatogr. 1996, 19, 2753-2765.
53. J. Blümel, Inorg. Chem. 1994, 33, 5050-5056
54. J. Sommer, Y. Yang, D. Rambow, J. Blümel, Inorg. Chem. 2004, 43, 7561-7563.
55. Y. Carpenter, C. A. Dyker, N. Burford, M. D. Lumsden, A. Decken, J. Am. Chem. Soc. 2008, 130, 15732-15741.
56. J. Dupont, R. F. deSouza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3692
57. P. Wasserscheid, W. Keim, Angew. Chem. 2000, 112, 3926-3945
58. Angew. Chem. Int. Ed. 2000, 39, 3772-3789.
59. C. Emnet, K. M. Weber, J. A. Vidal, C. S. Consorti, A. M. Stuart, J. A. Gladysz, Adv. Synth. Catal. 2006, 348, 1625-1634
60. D. Mandal, M. Jurisch, C. S. Consorti, J. A. Gladysz, Chem. Asian J. 2008, 3, 1772-1782.
61. H. M. Yeo, B. J. Ryu, K. C. Nam, Org. Lett. 2008, 10, 2931-2934
62. T. W. Hudnall, Y.-M. Kim, M. W. P. Bebbington, D. Bourissou, F. P. Gabba, J. Am. Chem. Soc. 2008, 130, 10890-10891.
63. G. C. Welch, D. W. Stephan, J. Am. Chem. Soc. 2007, 129, 1880-1881
64. G. C. Welch, R. R. San Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124-1126.
65. J. W. Wiench, C. Michon, A. Ellern, P. Hazendonk, A. Iuga, R. J. Angelici, M. Pruski, J. Am. Chem. Soc. 2009, 131, 11801-11810.
66. D. J. Casper, A. V. Sklyarov, S. Hardcastle, T. L. Barr, F. H. Försterling, K. F. Surerus, M. M. Hossain, Inorg. Chim. Acta 2006, 359, 3129-3138.
67. st edn., Vols. 1-3 (Eds.:, J.G. deaVries, C.J. Elsevier,), Wiley-VCH, Weinheim, 2007
68. M. Wende, R. Meier, J. A. Gladysz, J. Am. Chem. Soc. 2001, 123, 11490, and references cited therein
69. Adv. Synth. Catal. 2003, 345, Special Issue on hydrogenation, including, e.g.
70. W. S. Knowles, Adv. Synth. Catal. 2003, 345, 3
71. R. Noyori, Adv. Synth. Catal. 2003, 345, 15
72. T. Imamoto, Adv. Synth. Catal. 2003, 345, 79
73. D. M. Heinekey, A. Lledõs, J. M. Lluch, Chem. Soc. Rev. 2004, 33, 175-182.
74. D. Rutherford, J. J. J. Juliette, Ch. Rocaboy, I. T. Horváth, J. A. Gladysz, Catal. Today 1998, 42, 381-388.
75. E. Renaud, M. C. Baird, J. Chem. Soc. Dalton Trans. 1992, 2, 2905-2906
76. J. M. Buriak, J. C. Klein, D. G. Herrington, J. A. Osborn, Chem. Eur. J. 2000, 6, 139-150.
77. J. P. Collman, K. M. Kosydar, M. Bressan, W. Lamanna, T. Garrett, J. Am. Chem. Soc. 1984, 106, 2569-2579.
78. H. Gao, R. J. Angelici, Organometallics 1999, 18, 989-995.
79. D. R. Anton, R. H. Crabtree, Organometallics 1983, 2, 855-859.
80. M. Äapka, J. Hetflejs, V. M Vdovin, V. E. Fedorov, N. A. Pritula, G. K. Fedorova, React. Kinet. Catal. Lett. 1986, 31, 41-46
81. J. F. Biellmann, M. J. Jung, J. Am. Chem. Soc. 1968, 90, 1673-1674.
82. K. J. Stanger, Y. Tang, J. Anderegg, R. J. Angelici, J. Mol. Catal. A 2003, 202, 147-161.
83. L. Barthe, A. Denicourt-Nowicki, A. Roucoux, K. Philippot, B. Chaudret, M. Hemati, Catal. Commun. 2009, 10, 1235-1239
84. V. Mévellec, A. Nowicki, A. Roucoux, C. Dujardin, P. Granger, E. Payen, K. Philippot, New J. Chem. 2006, 30, 1214-1219
85. H. Beyer, K. Chatziapostolou, K. Köhler, Top. Catal. 2009, 52, 1752-1756
86. A. Roucoux, A. Novicky, K. Philippot, Nanopart. Catal. 2008, 349-388
87. L. Starkey Ott, R. G. Finke, Coord. Chem. Rev. 2007, 251, 1075-1100.