Ruthenium(II) half-sandwich complexes containing thioamides: Synthesis, structures and catalytic transfer hydrogenation of ketones

Journal of Organometallic Chemistry

Volumn 723, Issue , 2013, Pages 26-35

  Pandiarajan, Devaraj ^a   Ramesh, Rengan ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

Catalytic transfer hydrogenation; Crystal structure; Ruthenium(II) arene complex; Thioamide ligand

Indexed keywords

ACTIVE CATALYST; AIR STABLE; ARENE COMPLEXES; AROMATIC KETONES; CATALYST LOADINGS; CATALYTIC TRANSFER HYDROGENATION; CHLOROFORM SOLUTIONS; HALF-SANDWICH COMPLEXES; LIGAND-BASED TRANSITIONS; METAL CENTERS; METAL TO LIGAND CHARGE TRANSFERS; PIANO STOOL GEOMETRY; REACTION TEMPERATURE; SECONDARY ALCOHOLS; SINGLE CRYSTAL X-RAY CRYSTALLOGRAPHY; TETRAPHENYLBORATES; THIOAMIDES; TRANSFER HYDROGENATIONS; X-RAY DIFFRACTION METHOD;

CATALYSTS; CHARGE TRANSFER; CRYSTAL STRUCTURE; DYES; HYDROGENATION; KETONES; LIGANDS; LOADING; ORGANIC COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

SYNTHESIS (CHEMICAL);

EID: 84868563317     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2012.10.003     Document Type: Article

References (82)

1. P. Metzner Top. Curr. Chem. 204 1999 127 181
2. X.L. Geng, J. Wang, G.X. Li, P. Chen, S.F. Tian, and J. Qu J. Org. Chem. 73 2008 8558 8562
3. Y. Suzuki, R. Yazaki, N. Kumagai, and M. Shibasaki Angew. Chem. Int. Ed. 48 2009 5026 5029
4. T.J. Brown, R.F. Chapman, D.C. Cook, T.W. Hart, I.M. McLay, R. Jordan, J.S. Mason, M.N. Palfreyman, and R.J.A. Walsh J. Med. Chem. 35 1992 3613 3624
5. J.H. Miwa, A.K. Patel, N. Vivatrat, S.M. Popek, and A.M. Meyer Org. Lett. 3 2001 3373 3375
6. J.H. Miwa, L. Pallivathucal, S. Gowda, and K.E. Lee Org. Lett. 4 2002 4655 4657
7. C.C. Hughes, J.B. MacMillan, S.R. Gaudencio, P.R. Jensen, and W. Fencial Angew. Chem. Int. Ed. 48 2009 725 732
8. J. Zabicky The Chemistry of Amides 1970 Interscience New York
9. L. Delaude, A. Demonceau, and A.F. Noels Curr. Org. Chem. 10 2006 203 215
10. N. Chatani Sci. Synth. 1 2002 931 972
11. C. Scolaro, A. Bergamo, L. Brescacin, R. Delfino, M. Cocchietto, G. Laurenczy, T.J. Geldbach, G. Sava, and P.J. Dyson J. Med. Chem. 48 2005 4161 4171
12. H. Chen, J.A. Parkinson, R.E. Morris, and P.J. Sadler J. Am. Chem. Soc. 125 2003 173 186
13. H. Chen, J.A. Parkinson, S. Parsons, R.A. Coxall, R.O. Gould, and P.J. Sadler J. Am. Chem. Soc. 124 2002 3064 3082
14. R.E. Aird, J. Cummings, A.A. Ritche, M. Muir, R.E. Morris, H. Chen, P.J. Sadler, and D.I. Jodrell Br. J. Cancer 86 2002 1652 1657
15. R.E. Morris, R.E. Aird, P.S. Murdoch, H. Chen, J. Cummings, N.D. Hughes, A. Parsons, A. Parkin, G. Boyd, D.I. Jodrell, and P.J. Sadler J. Med. Chem. 44 2001 3616 3621
16. L.D. Dale, J.H. Tocher, T.M. Dyson, D.I. Edwards, and D.A. Tocher Anti-cancer Drug Des. 7 1992 3 14
17. E.O. Fischer, and R. Bottcher Z. Anorg. Allgem. Chem. 291 1957 305 309
18. M.A. Bennett, T.N. Huang, A.K. Smith, and T.W. Turney J. Chem. Soc. Chem. Commun. 1978 582 583
19. T.J. Geldbach, G. Laurenczy, R. Scopelliti, and P.J. Dyson Organometallics 25 2006 733 742
20. M. Tokunaga, and Y. Wakatsuki Angew. Chem. Int. Ed. 37 1998 2867 2869
21. C.A. Merlic, and M.E. Pauly J. Am. Chem. Soc. 118 1996 11319 11320
22. F. Simal, A. Demonceau, and A.F. Noels Angew. Chem. Int. Ed. 38 1999 538 540
23. N.E. Leadbeater, K.A. Scott, and L.J. Scott J. Org. Chem. 65 2000 3231 3232
24. H.D. Hansen, and J.H. Nelson Organometallics 19 2000 4740 4755
25. E. Bustelo, and P.H. Dixneuf Adv. Synth. Catal. 347 2005 393 397
26. Y. Wang, X. Li, and K. Ding Tetrahedron Lett. 43 2002 159 161
27. S. Urgaonkar, and J.G. Verkade Adv. Synth. Catal. 346 2004 611 616
28. B. Cetinkaya, I. Ozdemir, C. Bruneau, and P.H. Dixneuf Eur. J. Inorg. Chem. 2000 29 32
29. I. Ozdemir, E. Cetinkaya, B. Cetinkaya, M. Cicek, D. Semeril, C. Bruneau, and P.H. Dixneuf Eur. J. Inorg. Chem. 2004 418 422
30. C. Saluzzo, J. Breuzard, S. Pellet-Rostaing, M. Vallet, F.L. Guyader, M. Lemaire, and P. New J. Organomet. Chem. 643-644 2002 98 104
31. R.C. Larock Comprehensive Organic Transformations 1989 VCH New York p. 411
32. G.W. Kabalka, and R.S. Verma B.M. Trost, I. Flemings, Comprehensive Organic Synthesis vol. 8 1991 Pergamon Press Oxford 363
33. T. Ohkuma, M. Koizumi, K. Muniz, G. Hilt, C. Kabuto, and R. Noyori J. Am. Chem. Soc. 124 2002 6508 6509
34. K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, and R. Noyori Angew. Chem. Int. Ed. 38 1999 495 497
35. H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A.F. England, T. Ikariya, and R. Noyori Angew. Chem. Int. Ed. 37 1998 1703 1707
36. T. Ohkuma, H. Ooka, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 117 1995 10417 10418
37. R. Noyori, and T. Ohkuma Angew. Chem. Int. Ed. Engl. 40 2001 40 73
38. G. Zassinovich, G. Mestroni, and S. Gladiali Chem. Rev. 92 1992 1051 1069
39. R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 Wiley New York
40. T. Ohkuma, and R. Noyori E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis I-III vol. 1 1999 Springer-Verlag Berlin 199
41. I. Ojima Catalytic Asymmetric Synthesis second ed. 2000 Wiley New York
42. K. Everaere, A. Mortreux, and J.F. Carpentier Adv. Synth. Catal. 345 2003 67 77
43. J.S.M. Samec, J.E. Backvall, P.G. Andersson, and P. Brandt Chem. Soc. Rev. 35 2006 237 248
44. T. Ikariya, and A.J. Blacker Acc. Chem. Res. 40 2007 1300 1308
45. V. Caprio, and J.M.J. Williams Catalysis in Asymmetric Synthesis second ed. 2009 Wiley Chichester, UK
46. J.G. de Vries, and C.J. Elsevier Handbook of Homogeneous Hydrogenation 2006 Wiley-VCH Weinheim
47. S. Gladiali, and E. Alberico M. Beller, C. Bolm, Transition Metals for Organic Synthesis vol. 2 2004 Wiley-VCH Weinheim 145
48. S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 117 1995 7562 7563
49. W. Baratta, and P. Rigo Eur. J. Inorg. Chem. 2008 4041 4053
50. P. Braunstein, M.D. Fryzuk, F. Naud, and S.J. Rettig J. Chem. Soc. Dalton Trans. 1999 589 594
51. P. Braunstein, F. Naud, and S.J. Rettig New J. Chem. 25 2001 32 39
52. S. Ogo, T. Abura, and Y. Watanabe Organometallics 21 2002 2964 2969
53. M.T. Reetz, and X. Li J. Am. Chem. Soc. 128 2006 1044 1045
54. J.X. Gao, T. Ikariya, and R. Noyori Organometallics 15 1996 1087 1089
55. J.X. Gao, H. Zhang, X.D. Yi, P.P. Xu, C.L. Tang, H.L. Wan, K.R. Tsai, and T. Ikariya Chirality 12 2000 383 388
56. V. Rautenstrauch, X. Hoang-Cong, R. Churlaud, K. Abdur-Rashid, and R.H. Morris Chem. Eur. J. 9 2003 4954 4967
57. Z.R. Dong, Y.Y. Li, J.S. Chen, B.Z. Li, Y. Xing, and J.X. Gao Org. Lett. 7 2005 1043 1045
58. F. Zeng, and Z. Yu Organometallics 27 2008 6025 6028
59. W. Baratta, M. Ballico, A.D. Zotto, E. Herdtweck, S. Magnolia, R. Peloso, K. Siega, M. Toniutti, E. Zangrando, and P. Rigo Organometallics 28 2009 4421 4430
60. J.B. Sortais, V. Ritleng, A. Voelklin, A. Holuigue, H. Smail, L. Barloy, C. Sirlin, G.K.M. Verzijl, J.A.F. Boogers, A.H.M. de Vries, J.G. de Vries, and M. Pfeffer Org. Lett. 7 2005 1247 1250
61. D. Pandiarajan, and R. Ramesh Inorg. Chem. Commun. 14 2011 686 689
62. M.U. Raja, R. Ramesh, and K.H. Ahn Tetrahedron Lett. 50 2009 7014 7017
63. E. Sindhuja, R. Ramesh, and Y. Liu Dalton Trans. 41 2012 5351 5361
64. R.G. Hayter, and F.S. Humiec Inorg. Chem. 2 1963 306 312
65. R.D. Feltham, and R.G. Hayter J. Chem. Soc. 1964 4587 4591
66. W.J. Geary Coord. Chem. Rev. 7 1971 81 122
67. Y. Nojima, and M. Nonoyama Polyhedron 21 1996 3795 3809
68. S.K. Mandal, and A.R. Chakravarty J. Chem. Soc. Dalton Trans. 1992 1627 1633
69. F. Bernardi, L. Lunazzi, P. Zanirato, and G. Cerioni Tetrahedron 33 1977 1337 1340
70. F.B. McCormick, D.D. Cox, and W.B. Gleason Organometallics 12 1993 610 612
71. U. Beck, W. Hummel, H.B. Burgi, and A. Ludi Organometallics 6 1993 20 22
72. L. Wang, Q. Yang, H.Y. Fu, H. Chen, M.L. Yuan, and R.X. Li Appl. Organometal. Chem. 25 2011 626 631
73. M.C. Carrión, F.A. Jalón, B.R. Manzano, A.M. Rodríguez, F. Sepúlveda, and M. Maestro Eur. J. Inorg. Chem. 2007 3961 3973
74. M.C. Carrion, F. Sepulveda, F.A. Jalon, and B.R. Manzano Organometallics 28 2009 3822 3833
75. P. Kumar, M. Yadav, A.K. Singh, and D.S. Pandey Eur. J. Inorg. Chem. 2010 704 715
76. I. Nieto, M.S. Livings, J.B. Sacci, L.E. Reuther, M. Zeller, and E.T. Papish Organometallics 30 2011 6339 6342
77. S. Gladiali, and E. Alberico Chem. Soc. Rev. 35 2006 226 236
78. H.U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, and M. Studer Adv. Synth. Catal. 345 2003 103 151
79. D.D. perrin, and W.L.F. Armarego Purification of Laboratory Chemicals fourth ed. 1996 Butterworths-Heinemann London
80. M.A. Bennett, and A.K. Smith J. Chem. Soc. Dalton Trans. 1974 233 241
81. G.M. Sheldrick SHELXS 97, Program for the Solution of Crystal Structures 1997 University of Gottingen Germany
82. G.M. Sheldrick SHELXL 97, Program for the Refinement of Crystal Structures 1997 University of Gottingen Germany