Si-CN bond cleavage of silyl cyanides by an iron catalyst. A new route of silyl cyanide formation

Bulletin of the Chemical Society of Japan

Volumn 87, Issue 1, 2014, Pages 59-68

  Renzetti, Andrea ^a   Koga, Nobuaki ^b   Nakazawa, Hiroshi ^a  

^a Osaka Prefecture University   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CATALYSTS; CHEMICAL ACTIVATION; COORDINATION REACTIONS; CYANIDES; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILICON; SILICON CARBIDE;

C-N BOND CLEAVAGES; CATALYTIC AMOUNTS; CATALYTIC CYCLES; CO-ORDINATIVELY UNSATURATED; COORDINATED COMPLEXES; CYANIDE FORMATION; DFT CALCULATION; SILYL-MIGRATION;

IRON COMPOUNDS;

EID: 84986596604     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20130206     Document Type: Article

References (72)

1. a) S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068.
2. b) J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740.
3. c) A. Korotvicka, D. Necas, M. Kotora, Curr. Org. Chem. 2012, 16, 1170.
4. d) M. Tobisu, N. Chatani, Chem. Soc. Rev. 2008, 37, 300.
5. e) N. Chatani, Organomet. News 2009, 140.
6. f) E. Clot, O. Eisenstein, N. Jasim, S. A. Macgregor, J. E. McGrady, R. N. Perutz, Acc. Chem. Res. 2011, 44, 333.
7. g) T. Braun, F. Wehmeier, Eur. J. Inorg. Chem. 2011, 613.
8. h) H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119.
9. i) M. Klahn, U. Rosenthal,Organometallics 2012, 31, 1235.
10. j) C. Bianchini, A. Meli, F. Vizza, Eur. J. Inorg. Chem. 2001, 43.
11. k) H. K. Sharma, K. H. Pannell, Chem. Rev. 1995, 95, 1351.
12. l) S. Greenberg, D. W. Stephan, Chem. Soc. Rev. 2008, 37, 1482.
13. a) H. Nakazawa, T. Kawasaki, K. Miyoshi, C. H. Suresh, N. Koga, Organometallics 2004, 23, 117.
14. b) H. Nakazawa, K. Kamata, M. Itazaki, Chem. Commun. 2005, 4004.
15. c) H. Nakazawa, M. Itazaki, K. Kamata, K. Ueda, Chem. - Asian J. 2007, 2, 882.
16. a) K. Fukumoto, T. Oya, M. Itazaki, H. Nakazawa, J. Am. Chem. Soc. 2009, 131, 38.
17. b) A. A. Dahy, N. Koga, H. Nakazawa, Organometallics 2012, 31, 3995.
18. c) A. A. Dahy, N. Koga, H. Nakazawa, Organometallics 2013, 32, 2725.
19. K. Fukumoto, A. A. Dahy, T. Oya, K. Hayasaka, M. Itazaki, N. Koga, H. Nakazawa, Organometallics 2012, 31, 787.
20. J. Y. Corey, in The Chemistry of Organic Silicon Compounds Part 1, ed. by S. Patai, Z. Rappoport, John Wiley & Sons, New York, 2004, pp. 5-6.
21. Reaction in the NMR tube (in anhydrous solvent under nitrogen) was clean, affording only hydrosilane and silyl cyanide. No silanols or disiloxanes were observed by NMR spectroscopy. When the NMR tube was opened and the sample diluted under air for injection into the GC-MS instrument, both silyl cyanides hydrolyzed generating silanols and disiloxanes. These products were detected by GC-MS. Silanols and disiloxanes are not products of the metathesis reaction because they only formed after reaction upon exposure to air, not during the reaction under nitrogen.
22. a) R. P. Alexander, G. R. Stephenson, J. Organomet. Chem. 1986, 299, C1.
23. b) R. P. Alexander, T. D. James, G. R. Stephenson, J. Chem. Soc., Dalton Trans. 1987, 2013.
24. c) A. J. L. Pombeiro, D. L. Hughes, C. J. Pickett, R. L. Richards, J. Chem. Soc., Chem. Commun. 1986, 246.
25. d) S. S. P. R. Almeida, M. F. C. Guedes da Silva, J. J. R. Fraústoda Silva, A. J. L. Pombeiro, J. Chem. Soc., Dalton Trans. 1999, 467.
26. e) W. J. Evans, E. Montalvo, T. M. Champagne, J. W. Ziller, A. G. DiPasquale, A. L. Rheingold, Organometallics 2009, 28, 2897.
27. f) W. J. Evans, T. J. Mueller, J. W. Ziller, Chem. - Eur. J. 2010, 16, 964.
28. g) L. Zhang, C. W. Fung, K. S. Chan, Organometallics 2006, 25, 5381.
29. h) N. Chatani, T. Takeyasu, T. Hanafusa, Tetrahedron Lett. 1988, 29, 3979.
30. i) T. Pohlmann, A. de Meijere, Org. Lett. 2000, 2, 3877.
31. Y. Marcus, The Properties of Solvents, John Wiley & Sons, New York, 1998, pp. 95-102.
32. 2Me].
33. a) J. K. Rasmussen, S. M. Heilmann, L. R. Krepski, in Advances in Silicon Chemistry, ed. by G. L. Larson, JAI Press, Greenwich, CT, 1991, Vol. 1, pp. 65-187.
34. b) W. P. Weber, Silicon Reagents for Organic Synthesis in Reactivity and Structure Concepts in Organic Chemistry, Springer-Verlag, Berlin, 1983, Vol. 14. doi:10.1007/978-3-642-68661-0.
35. c) M. North, in Science of Synthesis: Houben Weyl Methods of Molecular Transformations, ed. by I. Fleming, Thieme, Stuttgart, 2002, Vol. 4, pp. 499-512.
36. M. North, D. L. Usanov, C. Young, Chem. Rev. 2008, 108, 5146.
37. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem., Int. Ed. 2004, 43, 788.
38. S. Hünig, G. Wehner, Synthesis 1979, 522.
39. J. K. Rasmussen, S. M. Heilmann, Synthesis 1979, 523.
40. K. Sukata, Bull. Chem. Soc. Jpn. 1987, 60, 2257.
41. M. T. Reetz, I. Chatziiosifidis, US Patent 4429145, 1984.
42. J. M. Aizpurua, C. Palomo, Nouv. J. Chim. 1984, 8, 51.
43. a) M. R. Booth, S. G. Frankiss, Chem. Commun. (London) 1968, 1347.
44. b) T. A. Bither, W. H. Knoth, R. V. Lindsey, Jr., W. H. Sharkey, J. Am. Chem. Soc. 1958, 80, 4151.
45. N. Koga, K. Morokuma, J. Am. Chem. Soc. 1988, 110, 108.
46. a) C. P. Casey, Transition Metal Organometallics in Organic Synthesis, ed. by H. Alper, Academic Press, New York, 1976, Vol. 1, pp. 190-193.
47. b) M. H. Chisholm, S. Godleski, Prog. Inorg. Chem. 1976, 20, 299.
48. c) C. G. Kreiter, V. Formáček, Angew. Chem., Int. Ed. Engl. 1972, 11, 141.
49. d) C. P. Casey, S. W. Polichnowski, J. Am. Chem. Soc. 1977, 99, 6097.
50. a) M. Itazaki, K. Ueda, H. Nakazawa, Angew. Chem. Int. Ed. 2009, 48, 3313
51. M. Itazaki, K. Ueda, H. Nakazawa, Angew. Chem. Int. Ed. 2009, 48, 6938.
52. b) M. Itazaki, M. Kamitani, K. Ueda, H. Nakazawa, Organometallics 2009, 28, 3601.
53. T. S. Piper, G. Wilkinson, J. Inorg. Nucl. Chem. 1956, 3, 104.
54. 2Me] was prepared according to the method in Ref. 22 by using methylcyclopentadiene.
55. R. B. King, W. M. Douglas, A. Efraty, J. Organomet. Chem. 1974, 69, 131.
56. S. R. Berryhill, B. Sharenow, J. Organomet. Chem. 1981, 221, 143.
57. C. Lo Sterzo, M. M. Miller, J. K. Stille, Organometallics 1989, 8, 2331.
58. B. F. Hallam, O. S. Mills, P. L. Pauson, J. Inorg. Nucl. Chem. 1955, 1, 313.
59. B. F. Hallam, P. L. Pauson, J. Chem. Soc. 1956, 3030.
60. J. P. Bibler, A. Wojcicki, J. Am. Chem. Soc. 1966, 88, 4862.
61. R. B. King, K. H. Pannel, Inorg. Chem. 1968, 7, 1510.
62. E. Scharrer, S. Chang, M. Brookhart, Organometallics 1995, 14, 5686.
63. 29Si NMR spectra due to its lower cost.
64. U. Hertenstein, S. Hünig, M. Öller, Chem. Ber. 1980, 113, 3783.
65. Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215.
66. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, (Revision C.01), Gaussian, Inc., Wallingford CT, 2009.
67. a) R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650.
68. b) A. J. H. Wachters, J. Chem. Phys. 1970, 52, 1033.
69. c) P. J. Hay, J. Chem. Phys. 1977, 66, 4377.
70. d) A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639.
71. a) K. Fukui, Acc. Chem. Res. 1981, 14, 363.
72. b) H. P. Hratchian, H. B. Schlegel, Theory and Applications of Computational Chemistry: The First 40 Years, ed. by C. E. Dykstra, G. Frenking, K. S. Kim, G. E. Scuseria, Elsevier, Amsterdam, 2005, pp. 195-249. doi:10.1016/B978-044451719-7/50053-6.