Crystal structure and computational investigation of an analogue of Grubbs' second generation catalyst with a fluorous phosphine

Inorganic Chemistry

Volumn 51, Issue 18, 2012, Pages 9943-9949

  Tuba, Robert ^a   Brothers, Edward N ^a   Reibenspies, Joseph H ^b   Bazzi, Hassan S ^a   Gladysz, John A ^b  

^a TEXAS A AND M UNIVERSITY AT QATAR   (Qatar)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FLUORINATED HYDROCARBON; ORGANOMETALLIC COMPOUND; PHOSPHINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, FLUORINATED; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; QUANTUM THEORY; RUTHENIUM;

EID: 84866411765     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic301434g     Document Type: Article

References (68)

1. Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley/VCH: Weinheim, Germany, 2004.
2. Fluorous Chemistry; Horváth, I. T., Ed.; Springer: Berlin, Germany, 2012; Topics in Current Chemistry, Vol. 308.
3. Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746-1787
4. Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. - Eur. J. 2001, 7, 3236-3253
5. Yao, Q.; Zhang, Y. J. Am. Chem. Soc. 2004, 126, 74-75
6. Krause, J. O.; Nuyken, O.; Buchmeiser, M. R. Chem. - Eur. J. 2004, 10, 2029-2035
7. Matsugi, M.; Curran, D. P. J. Org. Chem. 2005, 70, 1636-1642
8. Michalek, F.; Bannwarth, W. Helv. Chim. Acta 2006, 89, 1030-1037
9. Hensle, E. M.; Tobis, J.; Tiller, J. C.; Bannwarth, W. J. Fluorine Chem. 2008, 129, 968-973
10. Morton, D.; Leach, S.; Cordier, C.; Warriner, S.; Nelson, A. Angew. Chem., Int. Ed. 2009, 48, 104-109
11. Angew. Chem. 2009, 121, 110-115.
12. Matsugi, M.; Kobayashi, Y.; Suzumura, N.; Tsuchiya, Y.; Shioiri, T. J. Org. Chem. 2010, 75, 7905-7908
13. Correra da Costa, R. C.; Gladysz, J. A. Chem. Commun. 2006, 2619-2621
14. Correra da Costa, R.; Gladysz, J. A. Adv. Synth. Catal. 2007, 349, 243-254
15. GALGOQ, Lehman, S. E., Jr.; Wagener, K. B. Organometallics 2005, 24, 1477-1482
16. ICAQEK00, Samojłowicz, C.; Bieniek, M.; Pazio, A.; Makal, A.; Woźniak, K.; Poater, A.; Cavallo, L.; Wójcik, J.; Zdanowski, K.; Grela, K. Chem. - Eur. J. 2011, 17, 12981-12993
17. ITEHOF and ITEHIZ, Schmid, T. E.; Bantreil, X.; Citadelle, C. A.; Slawin, A. M. Z.; Cazin, C. S. J. Chem. Commun. 2011, 47, 7060-7062
18. NALTOK and NALTOK01 (two structures of an identical compound, 98 and 173 K), Day, M. W.; Trnka, T. M.; Grubbs, R. H. private communication to the CSD and reference 5a.
19. LIBKEN, Macnaughtan, M. L.; Johnson, M. J. A.; Kampf, J. W. Organometallics 2007, 26, 780-782
20. QOSMER, Yun, S. Y.; Kim, M.; Lee, D.; Wink, D. J. J. Am. Chem. Soc. 2008, 131, 24-25
21. Kromm, P.; Bideau, J.-P.; Cotrait, M.; Destrade, C.; Nguyen, H. Acta Crystallogr. 1994, C50, 112-115
22. Jablonski, C. R.; Zhou, Z. Can. J. Chem. 1992, 70, 2544-2551
23. Guillevic, M.-A.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1612-1615
24. Angew. Chem. 1997, 109, 1685-1687.
25. Guillevic, M.-A.; Rocaboy, C.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Organometallics 1998, 17, 707-717
26. Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M.; Cole-Hamilton, D. J.; Payne, M. J. J. Chem. Soc., Chem. Commun. 1997, 1127-1128
27. Haar, C. M.; Huang, J.; Nolan, S. P.; Petersen, J. L. Organometallics 1998, 17, 5018
28. Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russel, D. R.; Stuart, A. M.; Stuart, M. J. Chem. Soc., Dalton Trans. 1998, 3751-3764
29. Smith, D. C., Jr.; Stevens, E. D.; Nolan, S. P. Inorg. Chem. 1999, 38, 5277-5281
30. Stibrany, R. T.; Gorun, S. M. J. Organomet. Chem. 1999, 579, 217-221
31. Fawcett, J.; Hope, E. G.; Russel, D. R.; Stuart, A. M.; Wood, D. R. W. Polyhedron 2001, 20, 321-326
32. Croxtall, B.; Fawcett, J.; Hope, E. G.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 2002, 491-499
33. Adams, D. J.; Gudmunsen, D.; Fawcett, J.; Hope, E. G.; Stuart, A. M. Tetrahedron 2002, 58, 3827-3834
34. de Wolf, E.; Spek, A. L.; Kuipers, B. W. M.; Philipse, A. P.; Meeldijk, J. D.; Bomans, P. H. H.; Frederik, P. M.; Deelman, B.-J.; van Koten, G. Tetrahedron 2002, 58, 3911-3922
35. Malosh, T. J.; Wilson, S. R.; Shapley, J. R. Inorg. Chim. Acta 2009, 362, 2849-2855
36. Malosh, T. J.; Wilson, S. R.; Shapley, J. R. J. Organomet. Chem. 2009, 694, 3331-3337
37. Correra da Costa, R.; Hampel, F.; Gladysz, J. Polyhedron 2007, 26, 581-588
38. Tuba, R.; Tesevic, V.; Dinh, L. V.; Hampel, F.; Gladysz, J. A. Dalton Trans. 2005, 2275-2283
39. Consorti, C. S.; Hampel, F.; Gladysz, J. A. Inorg. Chim. Acta 2006, 359, 4874-4884
40. Baker, R. J.; Colavita, P. E.; Murph, D. M.; Platts, J. A.; Wallis, J. D. J. Phys. Chem. A 2012, 116, 1435-1444
41. Tuba, R.; Correa da Costa, R.; Bazzi, H. S.; Gladysz, J. A. ACS Catalysis 2012, 2, 155-162
42. Adlhart, C.; Chen, P. J. Am. Chem. Soc. 2004, 126, 3496-3510
43. Tsipis, A. C.; Orpen, A. G.; Harvey, J. N. Dalton Trans. 2005, 2849-2858
44. Sabbagh, I. T.; Kaye, P. T. J. Mol. Struct: THEOCHEM 2006, 763, 37-42
45. Zhao, Y.; Truhlar, D. G. Org. Lett. 2007, 9, 1967-1970
46. Minenkov, Y.; Singstad, Å.; Occhipinti, G.; Jensen, V. R. Dalton Trans. 2012, 41, 5526-5541
47. Jiao, H.; Le Stang, S.; Soós, T.; Meier, R.; Kowski, K.; Rademacher, P.; Jafarpour, L.; Hamard, J.-B.; Nolan, S. P.; Gladysz, J. A. J. Am. Chem. Soc. 2002, 124, 1516-1523
48. Crabtree, R. H. The Organometallic Chemistry of the Transitions Metals, 5 th ed.; John Wiley & Sons: Hoboken, NJ, 2009; Chapter 4.2.
49. Bunn, C. W.; Howells, E. R. Nature (London) 1954, 174, 549-551
50. Dunitz, J. D.; Gavezzotti, A.; Schweizer, W. B. Helv. Chim. Acta 2003, 86, 4073-4092
51. Dunitz, J. D. ChemBioChem 2004, 5, 614-621
52. Kuduva, S. S.; Boese, R. Cambridge Crystallographic Data Centre, Deposition 220154 (2003), refcode OLAWUT.
53. Albinsson, B.; Michl, J. J. Phys. Chem. 1996, 100, 3418-3429
54. Watkins, E. K.; Jorgensen, W. L. J. Phys. Chem. A 2001, 105, 4118-4125
55. Jang, S. S.; Blanco, M.; Goddard, W. A., III; Caldwell, G.; Ross, R. B. Macromolecules 2003, 36, 5331-5341
56. Bondi, A. J. Phys. Chem. 1964, 68, 441-451
57. Williams, D. E.; Houpt, D. J. Acta Crystallogr. 1986, B42, 286-295
58. Casnati, A.; Liantonio, R.; Metrangolo, P.; Resnati, G.; Ungaro, R.; Ugozzoli, F. Angew. Chem., Int. Ed. 2006, 45, 1915-1918
59. Angew. Chem. 2006, 118, 1949-1952.
60. Casnati, A.; Cavallo, G.; Metrangolo, P.; Resnati, G.; Ugozzoli, F.; Ungaro, R. Chem. - Eur. J. 2009, 15, 7903-7912
61. Monde, K.; Miura, N.; Hashimoto, M.; Taniguchi, T.; Inabe, T. J. Am. Chem. Soc. 2006, 128, 6000-6001
62. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Parandekar, P. V.; Mayhall, N. J.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian Development Version, Revision H.21; Gaussian, Inc.: Wallingford, CT, 2010.
63. Chai, J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
64. Weigend, F.; Furche, R.; Ahlrichs, R. J. Chem. Phys. 2003, 119, 12753-12762
65. GADDS/SAINT; Bruker AXS Inc.: Madison, WI, 2012.
66. Sheldrick, G. M. SADABS, Program for Absorption Correction of Area Detector Frames; Bruker AXS Inc.: Madison, WI
67. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
68. Fox, A. G.; O'Keefe, M. A.; Tabbernor, M. A. Acta Crystallogr. 1989, A45, 786-793