Benzene and heterocyclic rings formation in cycloaddition reactions catalyzed by RuCp derivatives: DFT studies

Inorganica Chimica Acta

Volumn 374, Issue 1, 2011, Pages 24-35

  Calhorda, Maria José ^a   Costa, Paulo J ^a   Kirchner, Karl A ^b  

^a UNIVERSITY OF LISBON   (Portugal)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Cycloaddition; Cyclopentadienyl complexes; Cyclotrimerization; DFT calculations; Metallacyclopentatriene complexes; Ruthenium

Indexed keywords

ACETYLENE; CATALYSIS; CYCLOADDITION; ETHYLENE; LIGHTING; METALS; MOLECULES; REACTION INTERMEDIATES; RUTHENIUM;

CATALYTICALLY ACTIVE SPECIES; CYCLOADDITION REACTION; CYCLOCOTRIMERIZATION; CYCLOPENTADIENYL COMPLEXES; CYCLOTRIMERIZATION; DFT CALCULATION; METALLACYCLOPENTATRIENE COMPLEXES; UNSATURATED MOLECULES;

RUTHENIUM COMPOUNDS;

EID: 79960562918     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2011.03.062     Document Type: Review

References (77)

1. W. Reppe, O. Schlichting, K. Klager, and T. Toepel Liebigs Ann. Chem. 560 1948 3
2. W. Reppe, and W. Schweckendiek Liebigs Ann. Chem. 560 1948 104
3. K.P.C. Vollhardt, and R.G. Bergman J. Am. Chem. Soc. 96 1974 4996
4. K.P.C. Vollhardt Angew. Chem., Int. Ed. Engl. 23 1984 539
5. S. Niu, and M.B. Hall Chem. Rev. 100 2000 353
6. D. Suzuki, H. Urabe, and F. Sato J. Am. Chem. Soc. 123 2001 7925
7. O.V. Ozerov, F.T. Ladipo, and B.O. Patrick J. Am. Chem. Soc. 121 1999 7941
8. M. Murakami, H. Itami, and Y. Ito J. Am. Chem. Soc. 119 1997 7163
9. A. Takeda, A. Ohno, I. Kadota, V. Gevorgyan, and Y. Yamamoto J. Am. Chem. Soc. 119 1997 4547
10. B. Witulski, and T. Stengel Angew. Chem., Int. Ed. Engl. 38 1999 2426
11. S. Abbet, A. Sanchez, U. Heiz, W.-D. Schneider, A.M. Ferrari, G. Pacchioni, and N. Rösch J. Am. Chem. Soc. 122 2000 3453
12. J.T. Fletcher, and M.J. Therien J. Am. Chem. Soc. 122 2000 12393
13. Y. Yamamoto, R. Ogawa, and K. Itoh Chem. Commun. 2000 549
14. Y. Yamamoto, K. Yamashita, and Y. Harada Chem. Asian J. 5 2010 946
15. J.A. Teske, and A. Deiters Org. Lett. 10 2008 2195
16. Y. Yamamoto, H. Kitahara, R. Ogawa, H. Kawaguchi, K. Tatsumi, and K. Itoh J. Am. Chem. Soc. 122 2000 4310
17. Y. Yamamoto, H. Kitahara, R. Hattori, and K. Itoh Organometallics 17 1998 1910
18. Y. Yamamoto, H. Kitahara, R. Ogawa, and K. Itoh J. Org. Chem. 63 1998 9610
19. Y. Yamamoto, R. Ogawa, and K. Itoh J. Am. Chem. Soc. 123 2001 6189
20. Y. Yamamoto, H. Takagishi, and K. Itoh J. Am. Chem. Soc. 124 2002 6844
21. G. Scott, and V.V. Fokin Angew. Chem., Int. Ed. 47 2008 8285
22. V. Cadierno, S.E. Garcia-Garrido, and J. Gimeno J. Am. Chem. Soc. 128 2006 15094
23. K. Kirchner Monatsh. Chem 139 2008 337
24. K. Kirchner, M.J. Calhorda, R. Schmid, and L.F. Veiros J. Am. Chem. Soc. 125 2003 11721
25. M.J. Calhorda, K. Kirchner, and L.F. Veiros C.G. Screttas, B.R. Steele, Perspectives in Organometallic Chemistry 2003 The Royal Society of Chemistry Cambridge 111
26. G. Dazinger, M. Torres-Rodriguez, K. Kirchner, M.J. Calhorda, and P.J. Costa J. Organomet. Chem. 691 2006 4434
27. G. Dazinger, R. Schmid, and K. Kirchner New. J. Chem. 2004 153
28. R. Schmid, and K. Kirchner J. Org. Chem. 68 2003 8339
29. B. Dutta, B.F.E. Curchod, P. Campomanes, E. Solari, R. Scopelliti, U. Rothlisberger, and K. Severin Chem. Eur. J. 16 2010 8400
30. J.H. Hardesty, J.B. Koerner, T.A. Albright, and G.-Y. Lee J. Am. Chem. Soc. 121 1999 6055
31. E. Rüba, K. Mereiter, R. Schmid, V.N. Sapunov, K. Kirchner, H. Schottenberger, M.J. Calhorda, and L.F. Veiros Chem. Eur. J. 8 2002 3948
32. R. Schmid, and K. Kirchner Eur. J. Inorg. Chem. 2004 2609
33. E. Becker, V. Stingl, G. Dazinger, M. Puchberger, K. Mereiter, and K. Kirchner J. Am. Chem. Soc. 128 2006 6572
34. E. Becker, V. Stingl, K. Mereiter, and K. Kirchner Organometallics 25 2006 4166
35. E. Becker, V. Stingl, G. Dazinger, K. Mereiter, and K. Kirchner Organometallics 26 2007 1531
36. N. Agenet, V. Gandon, K.P.C. Volhardt, M. Malacria, and C. Aubert J. Am. Chem. Soc. 129 2007 8860
37. J.A. Varela, and C. Saá J. Organomet. Chem. 694 2009 143
38. A.A. Dahy, and N. Koga Bull. Chem. Soc. Jpn. 78 2005 781
39. A.A. Dahy, C.H. Suresh, and N. Koga Bull. Chem. Soc. Jpn. 78 2005 792
40. L. Orian, J.N.P. van Stralen, and F.M. Bickelhaupt Organometallics 26 2007 3816
41. M.O. Albers, P.J.A. de Waal, D.C. Liles, D.J. Robinson, E. Singleton, and M.B. Wiege J. Chem. Soc., Chem. Commun. 1986 1680
42. C. Ernst, O. Walter, E. Dinjus, S. Arzberger, and H. Görls J. Prakt. Chem. 341 1999 801
43. Y. Yamada, J. Mizutani, M. Kurihara, and H. Nishihara J. Organomet. Chem. 80 2001 637
44. L. Zhang, H. H.-Y. Sung, I.D. Williams, Z. Lin, and G. Jia Organometallics 27 2008 5122
45. Y. Yamamoto, K. Hata, T. Arakawa, and K. Itoh Chem. Commun. 2003 1290
46. M. Paneque, M.L. Poveda, N. Rendón, and K. Mereiter J. Am. Chem. Soc. 126 2004 1610
47. Y. Yamamoto, T. Arakawa, R. Ogawa, and K. Itoh J. Am. Chem. Soc. 125 2003 12143
48. J.A. Varela, S.G. Rubin, L. Castedo, and C. Saá J. Org. Chem. 73 2008 1320
49. E. Rüba, R. Schmid, K. Kirchner, and M.J. Calhorda J. Organomet. Chem. 682 2003 204
50. B.K. Campion, R.H. Heyn, and T. Don Tilley Organometallics 9 1990 1106
51. C. Gemel, A. LaPensée, K. Mauthner, K. Mereiter, R. Schmid, and K. Kirchner Monatsh. Chem. 128 1997 1189
52. M. Crocker, M. Green, A.G. Orpen, and D.M. Thomas J. Chem. Soc., Chem. Commun. 1984 1141
53. M. Crocker, M. Green, A.G. Orpen, H.P. Neumann, and C.J. Schaverien J. Chem. Soc., Chem. Commun. 1984 1351
54. M. Crocker, S.F.T. Froom, M. Green, K.R. Nagle, A.G. Orpen, and D.M. Thomas J. Chem. Soc., Dalton Trans. 1987 2803
55. M. Crocker, M. Green, K.R. Nagle, A.G. Orpen, H.P. Newmann, C.E. Morton, and C.J. Schaverien Organometallics 9 1990 1422
56. J.R. Fritch, and K.P.C. Vollhardt Angew. Chem., Int. Ed. 18 1979 409
57. G. Ville, and K.P.C. Vollhardt J. Am. Chem. Soc. 103 1981 5267
58. G. Ville, K.P.C. Vollhardt, and M.J. Winter Organometallics 3 1984 1177
59. L.F. Veiros, K. Kirchner, and M.J. Calhorda Chem. Eur. J. 10 2004 5860
60. J.L. Le Paih, S. Dérien, B. Demerseman, C. Bruneau, P.H. Dixneuf, L. Toupet, G. Dazinger, and K. Kirchner K. Chem. Eur. J. 11 2005 1312
61. Y. Yamamoto, T. Arakawa, and K. Itoh Organometallics 23 2004 3610
62. L. Orian, W.-J. van Zeist, and F.M. Bickelhaupt Organometallics 27 2008 4028
63. Y. Yamamoto, K. Kinpara, T. Saigoku, H. Takagishi, S. Okuda, H. Nishiama, and K. Itoh J. Am. Chem. Soc. 127 2005 605
64. P. Hong, and H. Yamazaki Tetrahedron Lett. 1977 1333
65. P. Hong, and H. Yamazaki Synthesis 1977 50
66. R.A. Earl, and K.P.C. Vollhardt J. Org. Chem. 49 1984 4786
67. P. Diversi, G. Ingrosso, A. Lucherini, and S. Malquori J. Mol. Catal. 40 1987 267
68. H. Hoberg, and B.W. Oster Synthesis 1982 324
69. H. Hoberg, and B.W. Oster J. Organomet. Chem. 234 1982 C35
70. H. Hoberg, and B.W. Oster J. Organomet. Chem. 235 1983 359
71. S.T. Flynn, S.E. Hasso-Henerson, and A.W. Parkins J. Mol. Catal. 32 1985 101
72. Y. Wakatsuki, and H. Yamazaki J. Chem. Soc., Chem. Commun. 1973 280
73. H. Yamazaki J. Synth. Org. Chem. Jpn. 45 1987 244
74. Y. Yamamoto, H. Takagishi, and K. Itoh Org. Lett. 13 2001 2117
75. Y. Yamamoto, H. Takagishi, and K. Itoh J. Am. Chem. Soc. 124 2002 28
76. J. Rodríguez-Otero, M.M. Montero-Campillo, and E.M. Cabaleiro-Lago J. Phys. Chem. A 112 2008 8116
77. C.H. Suresh, and N. Koga J. Phys. Chem. A 105 2001 5940