Synthesis, electronic structure, and alkene hydrosilylation activity of terpyridine and bis(imino)pyridine iron dialkyl complexes

Organometallics

Volumn 31, Issue 13, 2012, Pages 4886-4893

  Tondreau, Aaron M ^a   Atienza, Crisita Carmen Hojilla ^a   Darmon, Jonathan M ^a   Milsmann, Carsten ^a   Hoyt, Helen M ^e,f   Weller, Keith J ^b   Nye, Susan A ^b   Lewis, Kenrick M ^c   Boyer, Julie ^b   Delis, Johannes G P ^d   Lobkovsky, Emil ^e   Chirik, Paul J ^a  

^a PRINCETON UNIVERSITY   (United States)

^b Momentive Performance Materials Inc   (United States)

^c Momentive Performance Materials Inc   (United States)

^d Momentive Performance Materials Bv   (Netherlands)

^e Department of Obstetrics Gynecology   (United States)

^f KNOX COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1-OCTENE; ANTIFERROMAGNETIC COUPLING; CATALYTIC HYDROSILYLATION; DENSITY FUNCTIONAL THEORY CALCULATIONS; DIALKYL COMPLEXES; MAGNETOCHEMISTRY; OXAZOLINES; RADICAL ANIONS; SSBAUER SPECTROSCOPIES; TERPYRIDINES;

DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; FUNCTIONAL GROUPS; HYDROSILYLATION; IRON; IRON COMPOUNDS; NITROGEN COMPOUNDS; OLEFINS; ORGANIC POLYMERS; PYRIDINE; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

CHELATION;

EID: 84863655783     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om3004527     Document Type: Article

References (74)

1. Pukhnarevitch, V. B.; Lukevics, E.; Kopylova, L. I.; Voronkov, M. Perspectives of Hydrosilylation; Institute for Organic Synthesis: Riga, Latvia, 1992.
2. Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley Interscience: New York, 1989.
3. Marciniec, B. Coord. Chem. Rev. 2005, 249, 2374
4. Marciniec, B. New J. Chem. 1997, 21, 815
5. Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, U.K., 1992.
6. Markó, I. E.; Stérin, S.; Buisine, O.; Mignani, G.; Branlard, P.; Tinant, B.; Declercq, J.-P. Science 2002, 298, 204
7. Buisine, O.; Berthon-Gelloz, G.; Brière, J.-F.; Stérin, S.; Mignani, G.; Branlard, P.; Tinant, B.; Declercq, J.-P.; Markó, I. E. Chem. Commun. 2005, 3856
8. Hitchcock, P. B.; Lappert, M. F.; Warhurst, N. J. W. Angew. Chem., Int. Ed. 1991, 30, 483
9. Howell, A. J. Platinum Met. Rev. 2008, 52, 243
10. Chirik, P. J.; Wieghardt, K. Science 2010, 327, 794
11. Chirik, P. J. In Catalysis Without Precious Metals; Bullock, M., Ed.; Wiley-VCH: Weinheim, Germany, 2010.
12. Marciniec, B. Silicon Chem. 2002, 1, 155
13. Simons, R. S.; Tessier, C. A. Organometallics 1996, 15, 2604
14. Kagiuchi, F.; Tanaka, Y.; Chatani, S.; Murai, S. J. Organomet. Chem. 1993, 456, 45
15. Mitchner, J. C.; Wrighton, M. S. J. Am. Chem. Soc. 1981, 103, 551
16. Sanner, R. D.; Austin, R. G.; Wrighton, M. S.; Honnick, W. D.; Pittman, C. U. Inorg. Chem. 1979, 18, 928
17. Schroeder, M. A.; Wrighton, M. S. J. Organomet. Chem. 1977, 128, 345
18. Nesmeyanov, A. N.; Freidlina, R. Kh.; Chukovskaya, E. C.; Petrova, R. G.; Belyavsky, A. B. Tetrahedron 1962, 17, 61
19. Naumov, R. N.; Itazaki, M.; Kamitani, M.; Nakazawa, H. J. Am. Chem. Soc. 2012, 134, 804
20. Wu, J. Y.; Stanzl, B. N.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 13214
21. Bart, S. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2004, 126, 13794
22. Tondreau, A. M.; Atienza, C. C. H.; Weller, K. J.; Nye, S. A.; Lewis, K. M.; Delis, J. G. P.; Chirik, P. J. Science 2012, 335, 567
23. Russell, S. K.; Darmon, J. M.; Lobkovsky, E.; Chirik, P. J. Inorg. Chem. 2010, 49, 2782
24. Wile, B. M.; Trovitch, R. J.; Bart, S. C.; Tondreau, A. M.; Lobkovsky, E.; Milsmann, C.; Bill, E.; Wieghardt, K.; Chirik, P. J. Inorg. Chem. 2009, 48, 4190
25. Cámpora, J.; Naz, A. M.; Palma, P.; álvarez, E.; Reyes, M. L. Organometallics 2005, 24, 4878
26. Fernandez, I.; Trovitch, R. J.; Lobkovsky, E.; Chirik, P. J. Organometallics 2008, 27, 109
27. For a review on iron-catalyzed hydrosilylation of carbonyl compounds, see: Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282
28. Tondreau, A. M.; Darmon, J. M.; Wile, B. M.; Floyd, S. K.; Lobkovsky, E.; Chirik, P. J. Organometallics 2009, 28, 3928
29. Tondreau, A. M.; Lobkovsky, E.; Chirik, P. J. Org. Lett. 2008, 10, 2789
30. Portions of this work were previously described in the following patent applications: Delis, J. G. P.; Chirik, P. J.; Tondreau, A. M. US 2011/0009565A1 and WO 2011/006049A1.
31. Kamata, K.; Suzuki, A.; Nakai, Y.; Nakazawa, H. Organometallics 2012, 31, 3825
32. 4]. See: Reiff, W. M.; Erickson, N. E.; Baker, W. A., Jr. Inorg. Chem. 1969, 8, 2019
33. Scarborough, C. C.; Lancaster, K. M.; DeBeer, S.; Weyhermüller, T.; Sproules, S.; Wieghardt, K. Inorg. Chem. 2012, 51, 3718
34. Bowes, K. F.; Clark, I. P.; Cole, J. M.; Gourlay, M.; Griffin, A. M. E.; Mahon, M. F.; Parker, A. W.; Raithby, P. R.; Sparkes, H. A.; Towrie, M. CrystEngComm 2005, 269
35. Bessel, C. A.; See, R. F.; Jameson, D. L.; Churchill, M. R.; Takeuchi, T. J. Chem. Soc., Dalton Trans. 1992, 3223
36. Vlasse, M.; Rojo, T.; Beltran-Porter, D. Acta Crystallogr., Sect. C 1983, 560
37. Belyakova, Z. V.; Bochkarev, V. N.; Golubtsov, S. A.; Belikova, Z. V.; Yamova, M. S.; Ainshtein, A. A.; Baranova, G. G.; Efremova, L. A.; Popkov, K. K. Russ. J. Gen. Chem. 1972, 42, 858
38. Warning! Silane disproportionation is known to result in spontaneous ignition. See: Buchwald, S. L. Chem. Eng. News 1993, 71, 2
39. Crivello, J. V.; Fan, M. Macromol. Symp. 1994, 77, 413
40. Nesakumar, J. E; Kannan, G; Kumar, V; Leatherman, M; Rajaraman, S. K. U.S. Publ. Pat. 0255318, 2008.
41. Czech, A. M; Creamer, C. E. U.S. Patent 6,515,094, 2003.
42. Trovitch, R. J.; Lobkovsky, E.; Bouwkamp, M. W.; Chirik, P. J. Organometallics 2008, 27, 6264
43. Knijnenburg, Q.; Gambarotta, S.; Budzelaar, P. H. M. Dalton Trans. 2006, 5442
44. Bart, S. C.; Chlopek, K.; Bill, E.; Bouwkamp, M. W.; Lobkovsky, E.; Neese, F.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13901
45. Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175
46. Ciszewski, J. T.; Mikhaylov, D. Y.; Holin, K. V.; Kadirov, M.; Budnikova, Y. H.; Sinyashin, O.; Vicic, D. A. Inorg. Chem. 2011, 50, 8630
47. Kuehl, C. J.; Re, D.; Scott, B. L.; Morris, D. E.; John, K. D. Chem. Commun. 2003, 2336
48. Mehdoui, T.; Berthet, J.-C.; Thuéry, P.; Salmon, L.; Rivière, E.; Ephritikhine, M. Chem.-Eur. J. 2005, 11, 6994
49. Shelter, E. J.; Wu, R.; Scott, B. L.; Thompson, J. D.; Morris, D. E.; Kiplinger, J. L. Angew. Chem., Int. Ed. 2008, 47, 2993
50. Gütlich, P.; Bill, E.; Trautwein, A. X. Mössbauer Spectroscopy and Transition Metal Chemistry: Fundamentals and Applications; Springer: Heidelberg, 2011; pp 83-89.
51. Römelt, M.; Ye, S.; Neese, F. Inorg. Chem. 2009, 48, 784
52. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518
53. Neese, F. ORCA: An ab Initio, DFT and Semiempirical Electronic Structure Package, version 2.8, revision 2287; Institut für Physikalische und Theoretische Chemie, Universität Bonn: Bonn, Germany, November 2010.
54. Becke, A. D. J. Chem. Phys. 1986, 84, 4524
55. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
56. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785
57. Neese, F.; Solomon, E. I. In Magnetism: From Molecules to Materials; Miller, J. S.; Drillon, M., Eds.; Wiley: New York, 2002; Vol. 4, p 345.
58. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571
59. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829
60. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297
61. Eichkorn, K.; Weigend, F.; Treutler, O.; Ahlrichs, R. Theor. Chem. Acc. 1997, 97, 119
62. Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283
63. Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 242, 652
64. Neese, F.; Wennmohs, F.; Hansen, A.; Becker, U. Chem. Phys. 2009, 356, 98
65. Kossmann, S.; Neese, F. Chem. Phys. Lett. 2009, 481, 240
66. Neese, F. J. Comput. Chem. 2003, 24, 1740
67. Ginsberg, A. P. J. Am. Chem. Soc. 1980, 102, 111
68. Noodleman, L.; Peng, C. Y.; Case, D. A.; Mouesca, J. M. Coord. Chem. Rev. 1995, 144, 199
69. Kirchner, B.; Wennmohs, F.; Ye, S.; Neese, F. Curr. Opin. Chem. Biol. 2007, 11, 134
70. Neese, F. J. Phys. Chem. Solids 2004, 65, 781
71. Molekel: Advanced Interactive 3D-Graphics for Molecular Sciences. Available at http://www.cscs.ch/molkel/.
72. Neese, F. Inorg. Chim. Acta 2002, 337, 181
73. Sinnecker, S.; Slep, L. D.; Bill, E.; Neese, F. Inorg. Chem. 2005, 44, 2245
74. Römelt, M.; Ye, S.; Neese, F. Inorg. Chem. 2009, 48, 784