An acyclic imino-substituted silylene: Synthesis, isolation, and its facile conversion into a zwitterionic silaimine

Angewandte Chemie - International Edition

Volumn 51, Issue 34, 2012, Pages 8589-8593

  Inoue, Shigeyoshi ^a   Leszczyńska, Kinga ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

carbenes; density functional calculations; silicon; silylenes; X ray structures

Indexed keywords

CARBENES; FACILE CONVERSION; NITROGEN ATOM; SILYLENES; X-RAY CRYSTALLOGRAPHIC STRUCTURES; X-RAY STRUCTURE; ZWITTERIONIC RESONANCE STRUCTURES;

DENSITY FUNCTIONAL THEORY; SILICON;

LIGANDS;

CARBENE; DRUG DERIVATIVE; IMINO ACID; METHANE; NITROGEN; SILICON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; IMINO ACIDS; METHANE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROGEN; SILICON;

EID: 84865065015     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203257     Document Type: Article

References (99)

1. M. Asay, C. Jones, M. Driess, Chem. Rev. 2011, 111, 354
2. S. Yao, Y. Xiong, M. Driess, Organometallics 2011, 30, 1748
3. V. Ya. Lee, A. Sekiguchi, Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb: From Phantom Species to Stable Compounds, Wiley, Chichester, 2010; pp. 139-188
4. M. Kira, Chem. Commun. 2010, 46, 2893
5. Y. Mizuhata, T. Sasamori, N. Tokitoh, Chem. Rev. 2009, 109, 3479, and references cited therein.
6. M. Denk, R. Lennon, R. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner, N. Metzler, J. Am. Chem. Soc. 1994, 116, 2691.
7. S. S. Sen, S. Khan, S. Nagendran, H. W. Roesky, Acc. Chem. Res. 2012, 45, 578
8. S. K. Mandal, H. W. Roesky, Chem. Commun. 2010, 46, 6016.
9. B. Gehrhus, M. F. Lappert, J. Heinicke, R. Boese, D. Bläser, J. Chem. Soc. Chem. Commun. 1995, 1931
10. B. Gehrhus, P. B. Hitchcock, M. F. Lappert, Z. Anorg. Allg. Chem. 2005, 631, 1383
11. W. Li, N. J. Hill, A. C. Tomasik, G. Bikzhanova, R. West, Organometallics 2006, 25, 3802
12. M. Driess, S. Yao, M. Brym, C. van Wüllen, D. Lentz, J. Am. Chem. Soc. 2006, 128, 9628
13. C.-W. So, H. W. Roesky, J. Magull, R. B. Oswald, Angew. Chem. 2006, 118, 4052
14. Angew. Chem. Int. Ed. 2006, 45, 3948
15. L. Kong, H. Zhang, H. Song, C. Cui, Dalton Trans. 2009, 5444
16. A. C. Tomasik, A. Mitra, R. West, Organometallics 2009, 28, 378
17. D. Gau, T. Kato, N. Saffon-Merceron, F. P. Cossío, A. Baceiredo, J. Am. Chem. Soc. 2009, 131, 8762.
18. M. Kira, S. Ishida, T. Iwamoto, C. Kabuto, J. Am. Chem. Soc. 1999, 121, 9722
19. M. Asay, S. Inoue, M. Driess, Angew. Chem. 2011, 123, 9763
20. Angew. Chem. Int. Ed. 2011, 50, 9589.
21. G.-H. Lee, R. West, T. Müller, J. Am. Chem. Soc. 2003, 125, 8114.
22. P. Jutzi, A. Mix, B. Rummel, W. W. Schoeller, B. Neumann, H.-G. Stammler, Science 2004, 305, 849.
23. P. Jutzi, K. Leszczyńska, B. Neumann, W. W. Schoeller, H.-G. Stammler, Angew. Chem. 2009, 121, 2634
24. Angew. Chem. Int. Ed. 2009, 48, 2596
25. P. Jutzi, K. Leszczyńska, A. Mix, B. Neumann, B. Rummel, W. W. Schoeller, H.-G. Stammler, Organometallics 2010, 29, 4759.
26. A. V. Protchenko, K. H. Birjkumar, D. Dange, A. D. Schwarz, D. Vidovic, C. Jones, N. Kaltsoyannis, P. Mountford, S. Aldridge, J. Am. Chem. Soc. 2012, 134, 6500.
27. B. D. Rekken, T. M. Brown, J. C. Fettinger, H. M. Tuononen, P. P. Power, J. Am. Chem. Soc. 2012, 134, 6504.
28. Y. Wang, B. Quillian, P. Wie, Y. Xie, C. S. Wannere, R. B. King, H. F. Schaefer III, P. von R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2007, 129, 12412
29. D. Scheschkewitz, Angew. Chem. 2008, 120, 2021
30. Angew. Chem. Int. Ed. 2008, 47, 1995.
31. Y. Wang, Y. Xie, P. Wei, R. B. King, H. F. Schaefer III, P. von R. Schleyer, G. H. Robinson, Science 2008, 321, 1069.
32. A. Sidiropoulos, C. Jones, A. Stasch, S. Klein, G. Frenking, Angew. Chem. 2009, 121, 9881
33. Angew. Chem. Int. Ed. 2009, 48, 9701.
34. Y. Wang, Y. Xie, P. Wei, R. B. King, H. F. Schaefer III, P. von R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2008, 130, 14970
35. O. Back, G. Kuchebbeiser, B. Donnadieu, G. Bertrand, Angew. Chem. 2009, 121, 5638
36. Angew. Chem. Int. Ed. 2009, 48, 5530
37. O. Back, B. Donnadieu, P. Parameswaran, G. Frenking, G. Bertrand, Nat. Chem. 2010, 2, 369.
38. M. Y. Abraham, Y. Wang, Y. Xie, P. Wie, H. F. Schaefer III, P. von R. Schleyer, G. H. Robinson, Chem. Eur. J. 2010, 16, 432.
39. R. Kinjo, B. Donnadieu, G. Bertrand, Angew. Chem. 2010, 122, 6066
40. Angew. Chem. Int. Ed. 2010, 49, 5930
41. L. Weber, Angew. Chem. 2010, 122, 5965
42. Angew. Chem. Int. Ed. 2010, 49, 5829.
43. D. Martin, M. Soleilhavoup, G. Bertrand, Chem. Sci. 2011, 2, 389
44. Y. Wang, G. H. Robinson, Dalton Trans. 2012, 41, 337.
45. Y. Apeloig, K. Albrecht, J. Am. Chem. Soc. 1995, 117, 7263
46. Q. Wang, Y. H. Ding, C. C. Sun, J. Phys. Chem. A 2004, 108, 10602
47. I. Bhattacharyya, N. C. Bera, A. K. Das, Int. J. Quantum Chem. 2008, 108, 447
48. I. Bhattacharyya, A. K. Das, Struct. Chem. 2009, 20, 1099.
49. S. Yao, M. Brym, C. van Wüllen, M. Driess, Angew. Chem. 2007, 119, 4237
50. Angew. Chem. Int. Ed. 2007, 46, 4159
51. Y. Xiong, S. Yao, M. Driess, J. Am. Chem. Soc. 2009, 131, 7562
52. Y. Xiong, S. Yao, M. Driess, Dalton Trans. 2010, 39, 9282
53. S. Yao, Y. Xiong, M. Driess, Chem. Eur. J. 2010, 16, 1281
54. T. Muraoka, K. Abe, Y. Haga, T. Nakamura, K. Ueno, J. Am. Chem. Soc. 2011, 133, 15365.
55. M. Tamm, S. Randoll, T. Bannenberg, E. Herdtweck, Chem. Commun. 2004, 876
56. M. Tamm, S. Randoll, E. Herdtweck, N. Kleigrewe, G. Kehr, G. Erker, B. Rieger, Dalton Trans. 2006, 459
57. S. Randoll, P. G. Jones, M. Tamm, Organometallics 2008, 27, 3232
58. T. K. Panda, A. G. Trambitas, T. Bannenberg, C. G. Hrib, S. Randoll, P. G. Jones, M. Tamm, Inorg. Chem. 2009, 48, 5462
59. A. G. Trambitas, T. K. Panda, J. Jenter, P. W. Roesky, C. Daniliuc, C. G. Hrib, P. G. Jones, M. Tamm, Inorg. Chem. 2010, 49, 2435
60. A. G. Trambitas, T. K. Panda, M. Tamm, Z. Anorg. Allg. Chem. 2010, 636, 2156
61. B. Haberlag, X. Wu, K. Brandhorst, J. Grunenberg, C. G. Daniliuc, P. G. Jones, M. Tamm, Chem. Eur. J. 2010, 16, 8868
62. A. G. Trambitas, J. Yang, D. Melcher, C. G. Daniliuc, P. G. Jones, Z. Xie, M. Tamm, Organometallics 2011, 30, 1122
63. S. Zhang, M. Tamm, K. Nomura, Organometallics 2011, 30, 2712
64. A. Glöckner, T. Bannenberg, C. G. Daniliuc, P. G. Jones, M. Tamm, Inorg. Chem. 2012, 51, 4368.
65. T. R. Cundari, Chem. Rev. 2000, 100, 807.
66. P. Jutzi, Chem. Rev. 1986, 86, 983
67. P. Jutzi, G. Reumann, J. Chem. Soc. Dalton Trans. 2000, 2237
68. P. Jutzi, Pure Appl. Chem. 2003, 75, 483.
69. P. Jutzi, D. Kanne, M. Hursthouse, A. J. Howes, Chem. Ber. 1988, 121, 1299.
70. M. Tamm, D. Petrovic, S. Randoll, S. Beer, T. Bannenberg, P. G. Jones, J. Grunenberg, Org. Biomol. Chem. 2007, 5, 523
71. S. Beer, K. Brandhorst, C. G. Hrib, X. Wu, B. Haberlag, J. Grunenberg, P. G. Jones, M. Tamm, Organometallics 2009, 28, 1534.
72. CCDC 878453 (2), 878454 (3) and 878455 (5) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
73. P. Jutzi, A. Mix, B, Neumann, B. Rummel, W. W. Schoeller, H.-G. Stammler, A. B. Rozhenko, J. Am. Chem. Soc. 2009, 131, 12137.
74. N. Metzler, M. Denk, Chem. Commun. 1996, 2657.
75. R. S. Ghadwal, H. W. Roesky, S. Merkel, D. Stalke, Chem. Eur. J. 2010, 16, 85
76. R. Azhakar, G. Tavčar, H. W. Roesky, J. Hey, D. Stalke, Eur. J. Inorg. Chem. 2011, 475
77. M. Y. Abraham, Y. Wang, Y. Xie, P. Wei, H. F. Schaefer III, P. von R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2011, 133, 8874
78. S. M. I. Al-Rafia, A. C. Malcolm, R. McDonald, M. J. Ferguson, E. Rivard, Chem. Commun. 2012, 48, 1308.
79. S. Inoue, M. Ichinohe, A. Sekiguchi, Chem. Lett. 2008, 37, 1044
80. K. Takeuchi, M. Ikoshi, M. Ichinohe, A. Sekiguchi, J. Am. Chem. Soc. 2010, 132, 930
81. K. Takeuchi, M. Ichinohe, A. Sekiguchi, Organometallics 2011, 30, 2044.
82. M. Kaftory, M. Kapon, M. Botoshansky, The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.:, Z. Rappoport, Y. Apeloig,), Wiley, Chichester, 1998.
83. N. Wiberg, K. Schurz, G. Reber, G. Müller, J. Chem. Soc. Chem. Commun. 1986, 591
84. G. Reber, J. Riede, N. Wiberg, K. Schurz, G. Müller, Z. Naturforsch. B 1989, 44, 786
85. N. Wiberg, K. Schurz, G. Müller, J. Riede, Angew. Chem. 1988, 100, 979
86. Angew. Chem. Int. Ed. Engl. 1988, 27, 935
87. S. Walter, U. Klingebiel, D. Schmidt-Bäse, J. Organomet. Chem. 1991, 412, 319
88. D. Stalke, U. Pieper, S. Vollbrecht, U. Klingebiel, Z. Naturforsch. B 1990, 45, 1513
89. D. Grosskopf, L. Marcus, U. Klingebiel, M. Noltemeyer, Phosphorus Sulfur Silicon Relat. Elem. 1994, 97, 113
90. M. Denk, R. K. Hayashi, R. West, J. Am. Chem. Soc. 1994, 116, 10813
91. J. Niesmann, U. Klingebiel, M. Schäfer, R. Boese, Organometallics 1998, 17, 947
92. H.-W. Lemer, M. Bolte, K. Schurz, N. Wiberg, G. Baum, D. Fenske, J. W. Bats, M. Wagner, Eur. J. Inorg. Chem. 2006, 4998
93. T. Iwamoto, N. Ohnishi, Z. Gui, S. Ishida, H. Isobe, S. Maeda, K. Ohno, M. Kira, New J. Chem. 2010, 34, 1637
94. S. Khan, S. S. Sen, D. Kratzert, G. Tavčar, H. W. Roesky, D. Stalke, Chem. Eur. J. 2011, 17, 4283
95. S.-H. Zhang, H.-X. Yeong, C.-W. So, Chem. Eur. J. 2011, 17, 3490
96. R. S. Ghadwal, H. W. Roesky, K. Propper, B. Dittrich, S. Klein, G. Frenking, Angew. Chem. 2011, 123, 5486
97. Angew. Chem. Int. Ed. 2011, 50, 5374.
98. R. C. Fischer, P. P. Power, Chem. Rev. 2010, 110, 3877.
99. K. Takeuchi, M. Ikoshi, M. Ichinohe, A. Sekiguchi, J. Organomet. Chem. 2011, 696, 1156.