Synthesis of osmium and ruthenium complexes bearing dimethyl (S,S)-2,2′-(pyridine-2,6-diyl)-bis-(4,5-dihydrooxazol-4-carboxylate) ligand and application to catalytic H/D exchange

Journal of Molecular Catalysis A: Chemical

Volumn 339, Issue 1-2, 2011, Pages 17-23

  Young, Kenneth J H ^a   Lokare, Kapil S ^b   Leung, Chin Hin ^b   Cheng, Mu Jeng ^c   Nielsen, Robert J ^c   Petasis, Nicos A ^a   Goddard III, William A ^c   Periana, Roy A ^b  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

C H activation; Osmium; PyBox; Ruthenium

Indexed keywords

BASIC CONDITIONS; C-H ACTIVATION; DFT CALCULATION; DINUCLEAR; H/D EXCHANGE; POISSON-BOLTZMANN; PYBOX; RESTING STATE; RUTHENIUM COMPLEXES; THERMALLY STABLE;

ACETIC ACID; ACTIVATION ANALYSIS; BENZENE; CARBOXYLATION; CHELATION; LIGANDS; OSMIUM; RUTHENIUM; RUTHENIUM COMPOUNDS; X RAY DIFFRACTION;

CHLORINE COMPOUNDS;

EID: 79954582106     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2011.01.029     Document Type: Article

References (72)

1. J. Atzrodt, V. Derdau, T. Fey, and J. Zimmermann Angew. Chem. Int. Ed. 46 2007 7744 and references therein
2. S.R. Klei, J.T. Golden, T.D. Tilley, and R.G. Bergman J. Am. Chem. Soc. 124 2002 2092
3. B.L. Conley, W.J. Tenn III, K.J.H. Young, S. Ganesh, S. Meier, V. Ziatdinov, O. Mironov, J. Oxgaard, J. Gonzales, W.A. Goddard III, and R.A. Periana W.B. Tolman, Activation of Small Molecules 2006 Wiley-VCH Weinheim, Germany 235 and references therein
4. K.J.H. Young, J. Oxgaard, D.H. Ess, S.K. Meier, T. Stewart, W.A. Goddard III, and R.A. Periana Chem. Commun. 2009 3270
5. C. Jia, T. Kitamura, and Y. Fujiwara Acc. Chem. Res. 34 2001 633
6. M. Muehlhofer, T. Strassner, and W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1745
7. J.A. Labinger, and J.E. Bercaw Nature 417 2002 507
8. R.H. Crabtree J. Chem. Soc. Dalton Trans. 2001 2437 and references therein
9. B. Hashiguchi, K.J.H. Young, M. Yousufuddin, W.A. Goddard III, and R.A. Periana J. Am. Chem. Soc. 132 2010 12542
10. D.H. Ess, R.J. Nielsen, W.A. Goddard III, and R.A. Periana J. Am. Chem. Soc. 131 2009 11686
11. S.K. Meier, K.J.H. Young, D.H. Ess, W.J. Tenn, J. Oxgaard, W.A. Goddard III, and R.A. Periana Organometallics 28 2009 5293
12. V.R. Ziatdinov, J. Oxgaard, O.A. Mironov, K.J.H. Young, W.A. Goddard III., and R.A. Periana J. Am. Chem. Soc. 128 2006 7404 and references therein
13. W.J. Tenn III, K.J.H. Young, J. Oxgaard, R.J. Nielsen, W.A. Goddard III, and R.A. Periana Organometallics 25 2006 5173
14. J.E. Bercaw, N. Hazari, J.A. Labinger, and P.F. Oblad Angew. Chem. Int. Ed. 47 2008 9941
15. S.K. Hanson, D.M. Heinekey, and K.I. Goldberg Organometallics 27 2008 1454
16. S.M. Kloek, D.M. Heinekey, and K.L. Goldberg Angew. Chem. Int. Ed. 46 2007 4736
17. G. Gerdes, and P. Chen Organometallics 23 2004 3031
18. J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325
19. For recent examples of early transition metal-Pybox catalysts
20. T. Inagaki, L.T. Phong, A. Furuta, J. Ito, and H. Nishiyama Chem. Eur. J. 16 2010 3090
21. M. Kawatsura, K. Kajita, S. Hayase, and T. Itoh Synlett 2010 1243
22. P.K. Singh, and V.K. Singh Org. Lett. 12 2010 80
23. For recent examples involving lanthanide-Pybox catalysts
24. G. Faita, M. Mella, M. Toscanini, and G. Desimoni Tetrahedron 66 2010 3024
25. H. Suga, S. Higuchi, M. Ohtsuka, D. Ishimoto, T. Arikawa, Y. Hashimoto, S. Misawa, T. Tsuchida, A. Kakehi, and T. Baba Tetrahedron 66 2010 3070
26. For a recent review, see: G. Desimoni, G. Faita, and P. Quadrelli Chem. Rev. 103 2003 3119
27. K. Nomura, W. Sidokmai, and Y. Imanishi Bull. Chem. Soc. Jpn. 73 2000 599
28. S. Iwasa, A. Fakhruddin, H.S. Widagdo, and H. Nishiyama Adv. Synth. Catal. 347 2005 517
29. S. Iwasa, K. Tajima, S. Tsushima, and H. Nishiyama Tetrahedron Lett. 42 2001 5897
30. M.K. Tse, S. Bhor, M. Klawonn, G. Anilkumar, H. Jiao, C. Döbler, A. Spannenberg, W. Mägerlein, H. Hugl, and M. Beller Chem. Eur. J. 12 2006 1855
31. M.K. Tse, C. Dobler, S. Bhor, M. Klawonn, W. Magerlein, H. Hugl, and M. Beller Angew. Chem. Int. Ed. 43 2004 5255
32. H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki, and K. Itoh Bull. Chem. Soc. Jpn. 68 1995 1247
33. H. Nishiyama, M. Kondo, T. Nakamura, and K. Itoh Organometallics 10 1991 500
34. H. Nishiyama Enantiomer 4 1999 569
35. H. Nishiyama, T. Shimada, H. Itoh, H. Sugiyama, and Y. Motoyama Chem. Commun. 1997 1863
36. S.B. Park, K. Murata, H. Matsumoto, and H. Nishiyama Tetrahedron: Asymmetry 6 1995 2487
37. D. Cuervo, M.P. Gamasa, and J. Gimeno Chem. Eur. J. 10 2004 425
38. J. Jankowska, J. Paradowska, B. Rakiel, and J. Mlynarski J. Org. Chem. 72 2007 2228
39. Y. Hisamatsu, K. Hasada, F. Amano, Y. Tsubota, Y. Wasada-Tsutsui, N. Shirai, S.-I. Ikeda, and K. Odashima Chem. Eur. J. 12 2006 7733
40. D.-H. Lee, B.P. Patel, E. Clot, O. Eisenstein, and R.H. Crabtree Chem. Commun. 1999 297
41. R.H. Crabtree, J.A. Loch, K. Gruet, D.-H. Lee, and C. Borgmann J. Organomet. Chem. 600 2000 7 22
42. A.D. Becke Phys. Rev. A 38 1988 3098
43. A.D. Becke J. Chem. Phys. 98 1993 5648
44. C.T. Lee, W.T. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
45. M.M. Francl, W.J. Pietro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. Defrees, and J.A. Pople J. Chem. Phys. 77 1982 3654
46. W.J. Hehre, R. Ditchfie, and J.A. Pople Chem. Phys. 56 1972 2257
47. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 299
48. Y. Zhao, and D.G. Truhlar Acc. Chem. Res. 41 2008 157
49. Y. Zhao, and D.G. Truhlar Theor. Chem. Acc. 120 2008 215
50. T. Clark, J. Chandrasekhar, G.W. Spitznagel, and P.V. Schleyer J. Comput. Chem. 4 1983 294
51. R. Krishnan, J.S. Binkley, R. Seeger, and J.A. Pople J. Chem. Phys. 72 1980 650
52. J.M.L. Martin, and A. Sundermann J. Chem. Phys. 114 2001 3408
53. NIST Chemistry WebBook. http://webbook.nist.gov/chemistry/ (retrieved 27.07.2010).
54. M.D. Tissandier, K.A. Cowen, W.Y. Feng, E. Gundlach, M.H. Cohen, A.D. Earhart, J.V. Coe, and T.R. Tuttle J. Phys. Chem. A 102 1998 7787
55. S. Iwasa, H. Nakamura, and H. Nishiyamam Heterocycles 52 2000 939
56. A thick wall glass rector sealed with a resealable PTFE valve
57. J.A. Cabeza, and P.M. Maitlis J. Chem. Soc. Dalton Trans. 1985 573
58. K.J.H. Young, S.K. Meier, J.M. Gonzales, J. Oxgaard, W.A. Goddard III, and R.A. Periana Organometallics 25 2006 4734 (supporting information)
59. G.M. Sheldrick SHELXTL, version 6.14 1997 Bruker Analytical X-ray System Inc. Madison, WI
60. R.H. Blessing Acta Crystallogr. A 51 1995 33
61. Internal Tables for Crystallographers, Vol. A, Space-Group Symmetry, D. Reidel Publishing Company, 1983, ISBN 90-277r-r1445-2.
62. Y. Feng, M. Lail, N.A. Foley, T.B. Gunnoe, K.A. Barakat, T.R. Cundari, and J.L. Petersen J. Am. Chem. Soc. 128 2006 7982
63. J. Oxgaard, W.J. Tenn, R.J. Nielsen, R.A. Periana, and W.A. Goddard III Organometallics 26 2007 1565
64. W.J. Tenn, K.J.H. Young, G. Bhalla, J. Oxgaard, W.A. Goddard III, and R.A. Periana J. Am. Chem. Soc. 127 2005 14172
65. Our attempt to optimize a stable ruthenium-benzene adduct which might precede CH activation led only to a 5-coordinate ruthenium complex and liberated benzene, suggesting no coordination barrier exists
66. A. Nutton, P.M. Bailey, and P.M. Maitlis J. Chem. Soc. Dalton Trans. 1981 1997
67. S. Cayemittes, T. Poth, M.J. Fernandez, P.G. Lye, M. Becker, H. Elias, and A.E. Merbach Inorg. Chem. 38 1999 4309
68. S.K. Meier, K.J.H. Young, D.H. Ess, W.J. Tenn III, J. Oxgaard, W.A. Goddard III, and R.A. Periana Organometallics 28 2009 5293
69. C.J. Jones, D. Taube, V.R. Ziatdinov, R.A. Periana, R.J. Nielsen, J. Oxgaard, and W.A. Goddard Angew. Chem. Int. Ed. 43 2004 4626
70. D.L. Davies, S.M.A. Donald, O. Al-Duaij, S.A. Macgregor, and M. Palleth J. Am. Chem. Soc. 128 2006 4210
71. D.L. Davies, S.M.A. Donald, and S.A. Macgregor J. Am. Chem. Soc. 127 2005 13754
72. D.H. Ess, S.M. Bischof, J. Oxgaard, R.A. Periana, and W.A. Goddard III Organometallics 27 2008 6440