Silylation of iron-bound carbon monoxide affords a terminal Fe carbyne

Journal of the American Chemical Society

Volumn 133, Issue 12, 2011, Pages 4438-4446

  Lee, Yunho ^a   Peters, Jonas C ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; BOND DISTANCE; CARBONYL COMPLEXES; CARBYNE COMPLEXES; CARBYNE LIGANDS; CARBYNES; CO LIGANDS; DATA POINTS; DFT CALCULATION; GEOMETRICAL CHANGES; HIGH-VALENT IRONS; IRON CENTERS; IRON COMPLEX; LOW-VALENT; MOSSBAUER; OXIDATION STATE; SILYL LIGANDS; SILYLATIONS; TETRADENTATE; TRIGONAL BIPYRAMIDAL GEOMETRY; XRD;

CARBON MONOXIDE; CARBONYLATION; ELECTRONIC STRUCTURE; INTERNET PROTOCOLS; LIGANDS; MOLYBDENUM COMPOUNDS; OXIDATION; X RAY DIFFRACTION;

IRON COMPOUNDS;

BARBAN; CARBON MONOXIDE; CARBONYL DERIVATIVE; IRON;

ARTICLE; ATOM; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; GEOMETRY; OXIDATION; SILYLATION; X RAY DIFFRACTION;

CARBAMATES; CARBON MONOXIDE; CRYSTALLOGRAPHY, X-RAY; IRON; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; SILICON COMPOUNDS; STEREOISOMERISM;

EID: 79953034897     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109678y     Document Type: Article

References (87)

1. Mindiola, D. J.; Hillhouse, G. L. J. Am. Chem. Soc. 2001, 123, 4623-4624
2. Jenkins, D. M.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2002, 124, 11238-11239
3. Brown, S. D.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2003, 125, 322-323
4. Dai, X. L.; Warren, T. H. J. Am. Chem. Soc. 2004, 126, 10085-10094
5. Ni, C. B.; Fettinger, J. C.; Long, G. J.; Brynda, M.; Power, P. P. Chem. Commun. 2008, 6045-6047
6. Shay, D. T.; Yap, G. P. A.; Zakharov, L. N.; Rheingold, A. L.; Theopold, K. H. Angew. Chem., Int. Ed. 2005, 44, 1508-1510
7. Ingleson, M. J.; Pink, M.; Fan, H.; Caulton, K. G. J. Am. Chem. Soc. 2008, 130, 4262-4267
8. Kieber-Emmons, M. T.; Riordan, C. G. Acc. Chem. Res. 2007, 40, 618-625
9. Kitiachvili, K. D.; Mindiola, D. J.; Hillhouse, G. H. J. Am. Chem. Soc. 2004, 126, 10554-10555
10. Lu, C. C.; Saouma, C. T.; Day, M. W.; Peters, J. C. J. Am. Chem. Soc. 2007, 129, 4-5
11. Laitar, D. S.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196-17197
12. Sadique, A. R.; Brennessel, W. W.; Holland, P. L. Inorg. Chem. 2008, 47, 784-786
13. Benson, E. E.; Kubiak, C. P.; Sathrum, A. J.; Smieja, J. M. Chem. Soc. Rev. 2009, 38, 89-99
14. Mankad, N. P.; Whited, M. T.; Peters, J. C. Angew. Chem., Int. Ed. 2007, 46, 5768-5771
15. Whited, M. T.; Mankad, N. P.; Lee, Y.; Oblad, P. F.; Peters, J. C. Inorg. Chem. 2009, 48, 2507-2517
16. Lee, Y; Mankad, N. P.; Peters, J. C. Nature Chem. 2010, 2, 558-565
17. Cummins, C. C. Chem. Commun. 1998, 1777-1786
18. Lee, C. L.; Hu, Y.; Ribbe, M. W. Science 2010, 642
19. Fischer, E. O.; Kreis, G.; Kreiter, C. G.; Müller, J.; Huttner, G.; Lorenz, H. Angew. Chem., Int. Ed. Engl. 1973, 12, 564
20. Transition Metal Carbyne Complexes; Kreissel, F. R., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1993.
21. Fischer, E. O.; Schneider, J.; Neugebauer, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 820-821 A related iron complex that was spectroscopically but not structurally characterized has also been described: Anderson, S.; Hill, A. F. J. Organomet. Chem. 1990, 394, C24-C26
22. Anderson, S.; Hill, A. F.; Ng, Y. T. Organometallics 2000, 19, 15-21
23. Joslin, F. L.; Stobart, S. R. J. Chem. Soc., Chem. Commun. 1989, 504-505
24. Hendriksen, D. E.; Oswald, A. A.; Ansell, G. B.; Leta, S.; Kastrup, R. V. Organometallics 1989, 8, 1153-1157
25. For examples of Fe(I)-CO species, see: Kisko, J. L.; Hascall, T.; Parkin, G. J. Am. Chem. Soc. 1998, 120, 10561-10562
26. MacBeth, D. E.; Harkins, S. B.; Peters, J. C. Can. J. Chem. 2005, 83, 332-340
27. Mock, M. T.; Popescu, C. V.; Yap, G. P. A.; Dougherty, W. G.; Riordan, C. G. Inorg. Chem. 2008, 47, 1889-1891
28. Addison, A. W.; Rao, T. N.; Reedijk, J.; Vanrijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356
29. Ayoko, G. A.; Eaborn, C.; Hitchcock, P. B. Organometallics 1995, 14, 4960-4961
30. Al-Juaid, S. S.; Al-Nasr, A. A.; Ayoko, G. A.; Eaborn, C.; Hitchcock, P. J. Organomet. Chem. 1995, 488, 155-160
31. Vrtis, R. N.; Rao, C. P.; Warner, S.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 2669-2670
32. Vrtis, R. N.; Liu, S.; Rao, S. P.; Bott, S. G.; Lippard, S. J. Organometallics 1991, 10, 275-285
33. Protasiewicz, J. D.; Masschelein, A.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 808-810
34. Sakaba, H.; Yoshida, M.; Kabuto, C.; Kabuto, K. J. Am. Chem. Soc. 2005, 127, 7276-7277
35. Stang, P. J.; Crittell, C. M.; Arif, A. M.; Karni, M.; Apeloig, Y. J. Am. Chem. Soc. 1991, 113, 7461-7470
36. Gleiter, R.; Werz, D. B.; Rominger, F.; Zhutov, E.; Zefirov, N. S.; Proskurnina, M. V. Eur. J. Org. Chem. 2007, 5834-5839
37. A Wiberg bond index analysis suggests strong multiple bond character in the Fe-C linkage (bond index = 1.85) and single bond character at the C-O linkage (bond index = 0.68) of 4. See Supporting Information for details.
38. Parkin, G. In Comprehensive Organometallic Chemistry; Crabtree, R. H.; Mingos, D. M. P., Eds.; Elsevier: Amsterdam, 2007; Vol. 1, pp 1 - 57.
39. Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2003, 125, 10782-10783
40. Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2004, 126, 6252-6254
41. Hendrich, M. P.; Gunderson, W.; Behan, R. K.; Green, M. T.; Mehn, M. P.; Betley, T. A.; Lu, C. C.; Peters, J. C. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 17107-17112
42. Thomas, C. M.; Mankad, N. P.; Peters, J. C. J. Am. Chem. Soc. 2006, 128, 4956-4957
43. Vogel, C.; Heinemann, F. W.; Sutter, J.; Anthon, C.; Meyer, K. Angew. Chem., Int. Ed. 2008, 47, 2681-2684
44. Scepaniak, J. J.; Young, J. A.; Bontchev, R. P.; Smith, J. M. Angew. Chem., Int. Ed. 2009, 48, 3158-3160
45. Detrich, J. L.; Konecny, R.; Vetter, W. M.; Doren, D.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 1996, 118, 1703-1712
46. Gibb, T. C. Principles of Mössbauer Spectroscopy; Wiley: New York, 1976.
47. Bancroft, G. M. Mössbauer Spectroscopy-An Introduction for Inorganic and Geochemists; McGraw-Hill: London, 1971.
48. Clark, M. G.; Cullen, W. R.; Garrod, R. E. B.; Maddock, A. G.; Sams, J. R. Inorg. Chem. 1973, 12, 1045
49. Pribula, C. G.; Brown, T. L.; Munck, E. J. Am. Chem. Soc. 1974, 96, 4149
50. Sosinsky, B. A.; Norem, N.; Shong, R. G. Inorg. Chem. 1982, 21, 4229-4233
51. Collins, R. L.; Pettit, R. J. Chem. Phys. 1963, 39, 3433
52. Sosinsky, B. A.; Norem, N.; Shong, R. G. Inorg. Chem. 1982, 21, 4229-4233
53. Dias, G. H. M.; Morigaki, M. K. Polyhedron 1992, 11, 1629-1636
54. Schmidt, G.; Balk, H. J. J. Organomet. Chem. 1974, 80, 257
55. +.
56. Feed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 899
57. Weinhold, F.; Landis, C. R. Valency and Bonding: A Natural Bond Ordital Donor-Acceptor Perspective; Cambridge University Press: New York, 2005.
58. Enemark, J. H.; Feltham, R. D. Coord. Chem. Rev. 1974, 13, 339-406
59. Richter-Addo, G. B.; Legzdin, P. Metal Nitrosyls; Oxford University Press: Oxford, UK, 1992.
60. Hill, A. F. Organometallics 2006, 25, 4741-4743
61. Parkin, G. Organometallics 2006, 25, 4744-4747
62. Figueroa, J. S.; Melnick, J. G.; Parkin, G. Inorg. Chem. 2006, 45, 7056-7058
63. Sircoglou, M.; Bontemps, S.; Bouhadir, G.; Saffon, N.; Miqueu, K.; Gu, W.; Mercy, M.; Chen, C.-H.; Foxman, B. M.; Maron, L.; Ozerov, O. V.; Bourissou, D. J. Am. Chem. Soc. 2008, 130, 16729-16738
64. Kuzu, I.; Krummenacher, I.; Meyer, J.; Armbruster, F.; Breher, F. Dalton Trans. 2008, 5836-5865
65. Braunschweig, H.; Dewhurst, R. D.; Schneider, A. Chem. Rev. 2010, 110, 3924-3957
66. Gualco, P.; Lin, T.-P.; Sircoglou, M.; Mercy, M.; Ladeira, S.; Bouhadir, G.; Pèrez, L. M.; Amgoune, A.; Maron, L.; Gabbaï, F.; Bourissou, D. Angew. Chem., Int. Ed. 2009, 48, 9892-9895
67. Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175-292
68. Pauling, L. J. Phys. Chem. 1952, 56, 361-365
69. Chen, Y.; Petz, W.; Frenking, G. Organometallics 2000, 19, 2698-2706
70. Krapp, A.; Pandey, K. K.; Frenking, G. J. Am. Chem. Soc. 2007, 129, 7596-7610
71. Schrock, R. R. J. Am. Chem. Soc. 1974, 96, 6796-6797
72. McLain, S. J.; Wood, C. D.; Messerle, L. W.; Schrock, R. R.; Hollander, F. J.; Youngs, W. J.; Churchill, M. R. J. Am. Chem. Soc. 1978, 100, 5962-5964
73. Mankad, N. P.; Müller, P.; Peters, J. C. J. Am. Chem. Soc. 2010, 132, 4083-4085
74. Peters, J. C.; Odom, A. L.; Cummins, C. C. J. Chem. Soc., Chem. Commun. 1997, 1995
75. Carlson, R. G.; Gile, M. A.; Heppert, J. A.; Mason, M. H.; Powell, D. R.; Velde, D. V.; Vilain, J. M. J. Am. Chem. Soc. 2002, 124, 1580-1581
76. Yakelis, N. A.; Bergman, R. G. Organometallics 2005, 24, 3579-3581
77. Brookhart, M.; Grant, B.; Volpe, A. F., Jr. Organometallics 1992, 11, 3920-3922
78. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122
79. Evans, D. F. J. Chem. Soc. 1959, 2003-2005
80. Sur, S. K. J. Magn. Reson. 1989, 82, 169-173
81. Neese, F. QCPE Bull. 1995, 15, 5
82. Feed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 899
83. Weinhold, F.; Landis, C. R. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: New York, 2005.
84. Frisch, M. J.; Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
85. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
86. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
87. 1H NMR spectrum.