Ruthenium cyclopentadienylidene phosphorane complexes - Synthesis, characterization and catalysis

Journal of Organometallic Chemistry

Volumn 767, Issue , 2014, Pages 165-176

  Kübler, Paul ^a   Oelkers, Benjamin ^a,b   Sundermeyer, Jörg ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b University of Koblenz Landau   (Germany)

Author keywords

Alkene alkyne coupling; Catalysis; Phosphorus ylide ligands; Ruthenium

Indexed keywords

CATALYSIS; HYDROCARBONS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

1-OCTYNE; COUPLING REACTION; ELECTRONIC EFFECTS; PHOSPHORANES; RUTHENIUM COMPLEXES; STERICALLY DEMANDING;

RUTHENIUM COMPOUNDS;

EID: 84903199525     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2014.06.002     Document Type: Article

References (88)

1. N.K. Hangaly, A.R. Petrov, K.A. Rufanov, K. Harms, M. Elfferding, and J. Sundermeyer Organometallics 30 2011 4544 4554
2. Z. Jian, N.K. Hangaly, W. Rong, Z. Mou, D. Liu, S. Li, A.A. Trifonov, J. Sundermeyer, and D. Cui Organometallics 31 2012 4579 4587
3. Z. Jian, A.R. Petrov, N.K. Hangaly, S. Li, W. Rong, Z. Mou, K.A. Rufanov, K. Harms, J. Sundermeyer, and D. Cui Organometallics 31 2012 4267 4282
4. F.G. Schröder, C. Lichtenberg, M. Elfferding, and J. Sundermeyer Organometallics 32 2013 5082 5091
5. A.R. Petrov, K.A. Rufanov, B. Ziemer, P. Neubauer, V.V. Kotov, and J. Sundermeyer Dalton Trans. 2008 909 915
6. A.R. Petrov, K.A. Rufanov, N.K. Hangaly, M. Elfferding, K. Harms, and J. Sundermeyer Mendeleev Commun. 20 2010 197 199
7. A.R. Petrov, M. Elfferding, J. Möbus, K. Harms, K.A. Rufanov, and J. Sundermeyer Eur. J. Inorg. Chem. 2010 4157 4165
8. C. Lichtenberg, N.S. Hillesheim, M. Elfferding, B. Oelkers, and J. Sundermeyer Organometallics 31 2012 4259 4266
9. H.W. Roesky, K. Swarat, and F. Edelmann Z. Naturforsch. 43b 1988 231 232
10. F. Otón, I. Ratera, A. Espinosa, K. Wurtz, T. Parella, A. Tárraga, J. Veciana, and P. Molina Chem. Eur. J. 16 2010 1532 1542
11. A. Ramos, and D.W. Stephan Dalton Trans. 39 2010 1328 1338
12. N. Lease, V. Vasilevski, M. Carreira, A. de Almeida, M. Sanaú, P. Hirva, A. Casini, and M. Contel J. Med. Chem. 56 2013 5806 5818
13. C. Freund, N. Barros, H. Gornitzka, B. Martin-Vaca, L. Maron, and D. Bourissou Organometallics 25 2006 4927 4930
14. J.H. Brownie, and M.C. Baird Coord. Chem. Rev. 252 2008 1734 1754
15. G.P. Sollott, H.E. Mertwoy, S. Portnoy, and J.L. Snead J. Org. Chem. 28 1963 1090 1092
16. W.E. McEwen, J.E. Fountaine, D.N. Schulz, and W.I. Shiau J. Org. Chem. 41 1976 1684 1690
17. C. Imrie, T.A. Modro, E.R. Rohwer, and C.C.P. Wagener J. Org. Chem. 58 1993 5643 5649
18. C. Imrie, T.A. Modro, and P.H. Van Rooyen Polyhedron 13 1994 1677 1682
19. P. Kübler, and J. Sundermeyer Dalton Trans. 43 2014 3750 3766
20. W. Simanko, W. Tesch, V.N. Sapunov, K. Mereiter, R. Schmid, K. Kirchner, J. Coddington, and S. Wherland Organometallics 17 1998 5674 5688
21. B.D. Swartz, and C. Nataro Organometallics 24 2005 2447 2451
22. K.G. Fowler, S.L. Littlefield, M.C. Baird, and P.H.M. Budzelaar Organometallics 30 2011 6098 6107
23. E. Ortega, N. Kleigrewe, G. Kehr, G. Erker, and R. Fröhlich Eur. J. Inorg. Chem. 2006 3769 3774
24. Review: B.M. Trost, M.U. Frederiksen, and M.T. Rudd Angew. Chem. Int. Ed. 44 2005 6630 6666
25. H.S. Chu, C.P. Lau, K.Y. Wong, and W.T. Wong Organometallics 17 1998 2768 2777
26. C. Standfest-Hauser, C. Slugovc, K. Mereiter, R. Schmid, K. Kirchner, L. Xiao, and W. Weissensteiner J. Chem. Soc. Dalton Trans. 2001 2989 2995
27. C.P. Casey, S.W. Singer, D.R. Powell, R.K. Hayashi, and M. Kavana J. Am. Chem. Soc. 123 2001 1090 1100
28. C. Hedberg, K. Källström, P.I. Arvidsson, P. Brandt, and P.G. Andersson J. Am. Chem. Soc. 127 2005 15083 15090
29. P.J. Fagan, M.H. Voges, and R.M. Bullock Organometallics 29 2010 1045 1048
30. B.M. Trost, A.B. Pinkerton, F.D. Toste, and M. Sperrle J. Am. Chem. Soc. 123 2001 12504 12509
31. K. Yamashita, Y. Yamamoto, and H. Nishiyama J. Am. Chem. Soc. 134 2012 7660 7663
32. B. Martín-Matute, K. Bogár, M. Edin, F.B. Kaynak, and J.-E. Bäckvall Chem. Eur. J. 11 2005 5832 5842
33. Y. Matsushima, H. Kikuchi, M. Uno, and S. Takahashi Bull. Chem. Soc. Jpn. 72 1999 2475 2482
34. D.S. Perekalin, E.A. Trifonova, V.V. Novikov, Y.V. Nelyubina, and A.R. Kudinov J. Organomet. Chem. 737 2013 21 25
35. S. Ding, L.-J. Song, L.W. Chung, X. Zhang, J. Sun, and Y.-D. Wu J. Am. Chem. Soc. 135 2013 13835 13842
36. B.M. Trost, and M.T. Rudd J. Am. Chem. Soc. 123 2001 8862 8863
37. B.M. Trost, and Z.T. Ball J. Am. Chem. Soc. 123 2001 12726 12727
38. R. Sebesta, I. Kmentova, and S. Toma Green Chem. 10 2008 484 496
39. B. Oelkers, and J. Sundermeyer Dalton Trans. 40 2011 12727 12741
40. M.J. Schneider, M. Haumann, M. Stricker, J. Sundermeyer, and P. Wasserscheid J. Catal. 309 2014 71 78
41. F. Ramirez, and S. Levy J. Anorg. Chem. Soc. 57 1957 6167 6172
42. B.M. Trost, and C.M. Older Organometallics 21 2002 2544 2546
43. E.P. Kündig, and F.R. Monnier Adv. Synth. Catal. 346 2004 901 904
44. A. Gutierrez, and T. Jamison J. Flow Chem. 1 2012 24 27
45. L. Quebatte, R. Scopelliti, and K. Severin Eur. J. Inorg. Chem. 16 2005 3353 3358
46. R.C. van der Drift, M. Gagliardo, H. Kooijman, A.L. Spek, E. Bouwman, and E. Drent J. Organomet. Chem. 690 2005 1044 1055
47. D. Duraczynska, and J.H. Nelson Dalton Trans. 2003 449 457
48. H. Suzuki, T. Kakigano, K.-i. Tada, M. Igarashi, K. Matsubara, A. Inagaki, M. Oshima, and T. Takao Bull. Chem. Soc. Jpn. 78 2005 67 87
49. E. Rüba, W. Simanko, K. Mauthner, K.M. Soldouzi, C. Slugovc, K. Mereiter, R. Schmid, and K. Kirchner Organometallics 18 1999 3843 3850
50. J.H. Brownie, M.C. Baird, and H. Schmider Organometallics 26 2007 1433 1443
51. J.H. Brownie, and M.C. Baird J. Organomet. Chem. 693 2008 2812 2817
52. L.A. Oro, M.A. Ciriano, M. Campo, C. Foces-Foces, and F.H. Cano J. Organomet. Chem. 289 1985 117 131
53. F.M. Conroy-Lewis, and S.J. Simpson J. Organomet. Chem. 322 1987 221 228
54. H. Hebbache, T. Jerphagnon, Z. Hank, C. Bruneau, and J.-L. Renaud J. Organomet. Chem. 695 2010 870 874
55. S. Manzini, C.A.U. Blanco, and S.P. Nolan Adv. Synth. Catal. 354 2012 3036 3044
56. L. Wang, Q. Yang, H.Y. Fu, H. Chen, M.-L. Yuan, and R.-X. Li Appl. Organomet. Chem. 25 2011 626 631
57. C. Scolaro, A.B. Chaplin, C.G. Hartinger, A. Bergamo, M. Cocchietto, B.K. Keppler, G. Sava, and P.J. Dyson Dalton Trans. 2007 5065 5072
58. A.B. Chaplin, and P.J. Dyson Organometallics 26 2007 2447 2455
59. F. Boeck, T. Kribber, L. Xiao, and L. Hintermann J. Am. Chem. Soc. 133 2011 8138 8141
60. A.B. Chaplin, and P.J. Dyson Organometallics 26 2007 4357 4360
61. J.A. Ayllon, S.F. Sayers, S. Sabo-Etienne, B. Donnadieu, B. Chaudret, and E. Clot Organometallics 18 1999 3981 3990
62. Y. Sun, H.-S. Chan, and Z. Xie Organometallics 25 2006 4188 4195
63. C.P. Casey, N.A. Strotman, S.E. Beetner, J.B. Johnson, D.C. Priebe, T.E. Vos, B. Khodavandi, and I.A. Guzei Organometallics 25 2006 1230 1235
64. C.P. Casey, N.A. Strotman, S.E. Beetner, J.B. Johnson, D.C. Priebe, and I.A. Guzei Organometallics 25 2006 1236 1244
65. A.R. Kudinov, M.I. Rybinskaya, Y.T. Struchkov, A.I. Yanovskii, and P.V. Petrovskii J. Organomet. Chem. 336 1987 187 197
66. P.G. Gassman, and C.H. Winter J. Am. Chem. Soc. 110 1988 6130 6135
67. A. Mercier, W.C. Yeo, J. Chou, P.D. Chaudhuri, G. Bernardinelli, and E.P. Kundig Chem. Commun. 2009 5227 5229
68. T.T. Co, S.C. Shim, C.S. Cho, T.-J. Kim, S.O. Kang, W.-S. Han, J. Ko, and C.-K. Kim Organometallics 24 2005 4824 4831
69. Z. Jian, W. Rong, Z. Mou, Y. Pan, H. Xie, and D. Cui Chem. Commun. 48 2012 7516 7518
70. K. Kirchner, K. Mereiter, K. Mauthner, and R. Schmid Inorg. Chim. Acta 217 1994 203 207
71. F. Grepioni, G. Cojazzi, D. Braga, E. Marseglia, L. Scaccianoce, and B.F.G. Johnson J. Chem. Soc. Dalton Trans. 1999 553 558
72. Z.L. Lutsenko, G.G. Aleksandrov, P.V. Petrovskii, E.S. Shubina, V.G. Andrianov, Y.T. Struchkov, and A.Z. Rubezhov J. Organomet. Chem. 281 1985 349 364
73. C. Gemel, K. Mereiter, R. Schmid, and K. Kirchner Organometallics 15 1996 532 542
74. M.R.J. Elsegood, and D.A. Tocher Polyhedron 14 1995 3147 3156
75. M.I. Bruce, F.S. Wong, B.W. Skelton, and A.H. White J. Chem. Soc. Dalton Trans. 1981 1398 1405
76. A. Trujillo, F. Justaud, L. Toupet, O. Cador, D. Carrillo, C. Manzur, and J.-R. Hamon New J. Chem. 35 2011 2027 2036
77. W. Luginbuehl, P. Zbinden, P.A. Pittet, T. Armbruster, H.B. Buergi, A.E. Merbach, and A. Ludi Inorg. Chem. 30 1991 2350 2355
78. D.B. Williams, M.E. Stoll, B.L. Scott, D.A. Costa, and J.W.J. Oldham Chem. Commun. 2005 1438 1440
79. C.P. Mehnert, R.A. Cook, N.C. Dispenziere, and E.J. Mozeleski Polyhedron 23 2004 2679 2688
80. A. Corma, H. García, and A. Leyva Tetrahedron 60 2004 8553 8560
81. T.J. Geldbach, G. Laurenczy, R. Scopelliti, and P.J. Dyson Organometallics 25 2005 733 742
82. W.L.F. Armarego, and D.D. Perrin Purification of Laboratory Chemicals 1996 Elsevier Burlington
83. M.A. Bennett, and A.K. Smith J. Chem. Soc. Dalton Trans. 1974 233 241
84. T.A. Stephenson, and G. Wilkinson J. Inorg. Nucl. Chem. 28 1966 945 956
85. STOE IPDS Software 1996 Stoe & Cie GmbH Darmstadt, Germany STOE X-AREA aN. D. X-RED, 2001, Stoe & Cie GmbH, Darmstadt, Germany
86. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837 838
87. A. Altomare, G. Cascarano, C. Giacovazzo, and A. Guagliardi J. Appl. Crystallogr. 26 1993 343 350
88. G.M. Sheldrick Acta Crystallogr. Sect. A Found. Crystallogr. 64 2007 112 122