N-heterocyclic carbene stabilized dichlorosilylene transition-metal complexes of V(I), Co(I), and Fe(0)

Inorganic Chemistry

Volumn 50, Issue 17, 2011, Pages 8502-8508

  Ghadwal, Rajendra S ^a   Azhakar, Ramachandran ^a   Pröpper, Kevin ^a   Holstein, Julian J ^a   Dittrich, Birger ^a   Roesky, Herbert W ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; METHANE; ORGANOMETALLIC COMPOUND; SILICON DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; METHANE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SILICON COMPOUNDS; STEREOISOMERISM; TRANSITION ELEMENTS;

EID: 80052221208     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic201096c     Document Type: Article

References (126)

1. Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91
2. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
3. Angew. Chem. 2002, 114, 1342-1363.
4. Liddle, S. T.; Edworthy, I. S.; Arnold, P. L. Chem. Soc. Rev. 2007, 36, 1732-1744
5. Kühl, O. Chem. Soc. Rev. 2007, 36, 592-607
6. Dragutan, V.; Dragutan, I.; Delaude, L.; Demonceau, A. Coord. Chem. Rev. 2007, 251, 765-794
7. Arnold, P. L.; Pearson, S. Coord. Chem. Rev. 2007, 251, 596-609
8. Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883
9. Jacobsen, H.; Correa, A.; Poater, A.; Costabile, C.; Cavallo, L. Coord. Chem. Rev. 2009, 253, 687-703
10. de Frémont, P.; Marion, N.; Nolan, S. P. Coord. Chem. Rev. 2009, 253, 862-892
11. Glorius, F. N-Heterocyclic Carbenes in Transition Metal Catalysis; Topics in Organometallic Chemistry; Springer-Verlag: Berlin, Germany, 2007, pp 1-218.
12. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122-3172
13. Angew. Chem. 2008, 120, 3166-3216.
14. McGuinness, D. Dalton Trans. 2009, 6915-6923
15. Wang, Y.; Quillian, B.; Wei, P.; Wannere, C. S.; Xie, Y.; King, R. B.; Schaefer, H. F., III; von R. Schleyer, P.; Robinson, G. H. J. Am. Chem. Soc. 2007, 129, 12412-12413
16. Masuda, J.; Schoeller, W. W.; Donnadieu, B.; Bertrand, G. J. Am. Chem. Soc. 2007, 129, 14180-14181
17. Masuda, J.; Schoeller, W. W.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2007, 46, 7052-7055
18. Angew. Chem. 2007, 119, 7182-7185.
19. Dyker, C. A.; Bertrand, G. Science 2008, 321, 1050-1051
20. Wang, Y.; Xie, Y.; Wei, P.; King, R. B.; Schaefer, H. F., III; von R. Schleyer, P.; Robinson, G. H. Science 2008, 321, 1069-1071
21. Wang, Y.; Xie, Y.; Wei, P.; King, R. B.; Schaefer, H. F., III; von R. Schleyer, P.; Robinson, G. H. J. Am. Chem. Soc. 2008, 130, 14970-14971
22. Dyker, C. A.; Lavallo, V.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 3206-3209
23. Angew. Chem., Int. Ed. 2008, 120, 3250-3253.
24. Fürstner, A.; Alcarazo, M.; Goddard, R.; Lehmann, C. W. Angew. Chem., Int. Ed. 2008, 47, 3210-3214
25. Angew. Chem., Int. Ed. 2008, 120, 3254-3258.
26. Wang, Y.; Quillian, B.; Wei, P.; Xie, Y.; Wannere, C. S.; King, R. B.; Schaefer, H. F., III; von R. Schleyer, P.; Robinson, G. H. J. Am. Chem. Soc. 2008, 130, 3298-3299
27. Wang, Y.; Robinson, G. H. Chem. Commun. 2009, 5201-5213
28. Back, O.; Kuchenbeiser, G.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2009, 48, 5530-5533
29. Angew. Chem., Int. Ed. 2009, 121, 5638-5641.
30. Filippou, A. C.; Chernov, O.; Schnakenburg, G. Angew. Chem., Int. Ed. 2009, 48, 5687-5690
31. Angew. Chem. 2009, 121, 5797-5800.
32. Sidiropoulos, A.; Jones, C.; Stasch, A.; Klein, S.; Frenking, G. Angew. Chem., Int. Ed. 2009, 48, 9701-9704
33. Angew. Chem., Int. Ed. 2009, 121, 9881-9884.
34. Abraham, M. Y.; Wang, Y.; Xie, Y.; Wei, P.; Schaefer, H. F., III; von R. Schleyer, P.; Robinson, G. H. Chem.-Eur. J. 2010, 16, 432-435
35. Ghadwal, R. S.; Roesky, H. W.; Merkel, S.; Henn, J.; Stalke, D. Angew. Chem., Int. Ed. 2009, 48, 5683-5686
36. Angew. Chem., Int. Ed. 2009, 121, 5793-5796.
37. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541
38. Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988-3000
39. Angew. Chem., Int. Ed. 2007, 119, 3046-3058.
40. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606-5655
41. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29
42. Chauvin, Y. Angew. Chem., Int. Ed. 2006, 45, 3740-3747
43. Angew. Chem., Int. Ed. 2006, 118, 3824-3831.
44. Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760-3765
45. Angew. Chem. 2006, 118, 3845-3850.
46. Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748-3759
47. Angew. Chem., Int. Ed. 2006, 118, 3832-3844.
48. Tilley, T. D. In The Chemistry of Organosilicon Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1989; p 1415.
49. Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1991; p 245-308; p 309-364.
50. Ogino, H. Chem. Rec. 2002, 2, 291-306
51. Okazaki, M.; Tobita, H.; Ogino, H. Dalton Trans. 2003, 493-506
52. Waterman, R.; Hayes, P. G.; Tilley, T. D. Acc. Chem. Res. 2007, 40, 712-719
53. Zybill, C. E.; Liu, C. Synlett 1995, 687-699
54. Goikhman, R.; Milstein, D. Chem.-Eur. J. 2005, 11, 2983-2988
55. Schneider, N.; Finger, M.; Haferkemper, C.; Bellemin-Laponnaz, S.; Hofmann, P.; Gade, L. H. Chem.-Eur. J. 2009, 15, 11515-11529
56. Yamamoto, K.; Okinoshima, H.; Kumada, M. J. Organomet. Chem. 1970, 23, C7-C8
57. Yamamoto, K.; Okinoshima, H.; Kumada, M. J. Organomet. Chem. 1971, 27, C31-C32
58. Okinoshima, H.; Yamamoto, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9263-9264
59. Okinoshima, H.; Yamamoto, K.; Kumada, M. J. Organomet. Chem. 1975, 86, C27-C30
60. Aitken, C.; Harrod, J. F.; Gill, U. S. Can. J. Chem. 1987, 65, 1804-1809
61. Ojima, I.; Inaba, S.; Kogure, T. J. Organomet. Chem. 1973, 55, C7-C8
62. Pannell, K. H.; Wang, L.-J.; Rozell, J. M. Organometallics 1989, 8, 550-552
63. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1992, 11, 3227-3232
64. Pannell, K. H.; Cervantes, J.; Hernandez, C.; Cassias, J.; Vincenti, S. Organometallics 1986, 5, 1056-1057
65. Tobita, H.; Ueno, K.; Ogino, H. Chem. Lett. 1986, 1777-1780
66. Tobita, H.; Ueno, K.; Ogino, H. Bull. Chem. Soc. Jpn. 1988, 61, 2797-2804
67. Pannell, K. H.; Rozell, J. M., Jr.; Hernandez, C. J. Am. Chem. Soc. 1989, 111, 4482-4485
68. Haynes, A.; George, M. W.; Haward, M. T.; Poliakoff, M.; Turner, J. J.; Boag, N. M.; Green, M. J. Am. Chem. Soc. 1991, 113, 2011-2020
69. Gaspar, P. P.; West, R. In The Chemistry of Organic Silicon Compounds; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, U.K., 1998, Vol. 2; p 2463-2568.
70. Tokitoh, N.; Ando, W. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley: New York, 2004, p 651-715.
71. Gaspar, P. P. in Reactive Intermediates, Jones, M., Jr.; Moss, R. A., Eds.; Wiley: New York, 1985, Vol. 3, p 333-427.
72. Thorp, H. H. Science 2000, 289, 882-883
73. Laplaza, C. E.; Cummins, C. C. Science 1995, 268, 861-863
74. Baird, M. C.; Wilkinson, G. J. Chem. Soc Chem. Commun. 1966, 267-268
75. Clark, G. R.; James, S. M. J. Organomet. Chem. 1977, 134, 229-236
76. Clark, G. R.; Marsden, K.; Roper, W. R.; Wright, L. J. J. Am. Chem. Soc. 1980, 102, 1206-1207
77. Clark, G. R.; Marsden, K.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. J. Organomet. Chem. 1988, 338, 393-410
78. Klei, S. R.; Tilley, T. D.; Bergman, R. G. Organometallics 2002, 21, 4648-4661
79. Glaser, P. B.; Tilley, T. D. J. Am. Chem. Soc. 2003, 125, 13640-13641
80. Calimano, E.; Tilley, T. D. J. Am. Chem. Soc. 2008, 130, 9226-9227
81. Calimano, E.; Tilley, T. D. J. Am. Chem. Soc. 2009, 131, 11161-11173
82. Brunner, H. Angew. Chem., Int. Ed. 2004, 43, 2749-2750
83. Angew. Chem., Int. Ed. 2004, 116, 2805-2807.
84. Denk, M.; Hayashi, R. K.; West, R. J. Am. Chem. Soc. 1994, 116, 10813-10814
85. Schmedake, T. A.; Haaf, M.; Paradise, B. J.; Millevolte, A. J.; Powell, D.; West, R. J. Organomet. Chem. 2001, 636, 17-25
86. Haaf, M.; Hayashi, R.; West, R. J. Chem. Soc. D 1994, 33-34
87. West, R.; Denk, M. Pure Appl. Chem. 1996, 68, 785-788
88. Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F.; Maciejewski, H. Organometallics 1998, 17, 5599-5601
89. Petri, S. H. A.; Eikenberg, D.; Neumann, B.; Stammler, H.-G.; Jutzi, P. Organometallics 1999, 18, 2615-2618
90. Schmedake, T. A.; Haaf, M.; Paradise, B. J.; Powell, D.; West, R. Organometallics 2000, 19, 3263-3265
91. Clendenning, S. B.; Gehrhus, B.; Hitchcock, P. B.; Moser, D. F.; Nixon, J. F.; West, R. J. Chem. Soc., Dalton Trans. 2002, 484-490
92. Amoroso, D.; Haaf, M.; Yap, G. P. A.; West, R.; Fogg, D. E. Organometallics 2002, 21, 534-540
93. Avent, A. G.; Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F.; Maciejewski, H. J. Organomet. Chem. 2003, 686, 321-331
94. Haaf, M.; Schmedake, T. A.; West, R. Acc. Chem. Res. 2000, 33, 704-714
95. Azhakar, R.; Sarish, S. P.; Roesky, H. W.; Hey, J.; Stalke, D. Inorg. Chem. 2011, 50, 5039-5043
96. Yang, W.; Fu, H.; Wang, H.; Chen, M.; Ding, Y.; Roesky, H. W.; Jana, A. Inorg. Chem. 2009, 48, 5058-5060
97. Meltzer, A.; Präsang, C.; Driess, M. J. Am. Chem. Soc. 2009, 131, 7232-7233
98. Wang, W.; Inoue, S.; Yao, S.; Driess, M. J. Am. Chem. Soc. 2010, 132, 15890-15892
99. Li, J.; Merkel, S.; Henn, J.; Meindl, K.; Döring, A.; Roesky, H. W.; Ghadwal, R. S.; Stalke, D. Inorg. Chem. 2010, 49, 775-777
100. Tavčar, G.; Sen, S. S.; Azhakar, R.; Thorn, A.; Roesky, H. W. Inorg. Chem. 2010, 49, 10199-10202
101. Schmeisser, V. M.; Voss, P. Z. Anorg. Allg. Chem. 1964, 334, 50-56
102. Schenk, V. P. W.; Bloching, H. Z. Anorg. Allg. Chem. 1964, 334, 57-65
103. Timms, P. L. Inorg. Chem. 1968, 7, 387-389
104. Koe, J. R.; Powell, D. R.; Buffy, J. J.; Hayase, S.; West, R. Angew. Chem., Int. Ed. 1998, 37, 1441-1442
105. Angew. Chem., Int. Ed. 1998, 110, 1514-1515.
106. Leis, C.; Wilkinson, D. L.; Handwerker, H.; Zybill, C.; Müller, G. Organometallics 1992, 11, 514-529
107. Simons, R. S.; Tessier, C. A. Acta Crystallogr. 1996, C52, 840-842
108. Du, V. A.; Stipicic, G. N.; Bendova, M.; Schubert, U. Monatsh. Chem. 2010, 141, 671-675
109. Ghadwal, R. S.; Roesky, H. W.; Merkel, S.; Stalke, D. Chem.-Eur. J. 2010, 16, 85-88
110. Azhakar, R.; Tavčar, G.; Roesky, H. W.; Hey, J.; Stalke, D. Eur. J. Inorg. Chem. 2011, 475-477
111. Ghadwal, R. S.; Sen, S. S.; Roesky, H. W.; Granitzka, M.; Kratzert, D.; Merkel, S.; Stalke, D. Angew. Chem., Int. Ed. 2010, 49, 3952-3955
112. Angew. Chem., Int. Ed. 2010, 122, 4044-4047.
113. Ghadwal, R. S.; Roesky, H. W.; Schulzke, C.; Granitzka, M. Organometallics 2010, 29, 6329-6333
114. Ghadwal, R. S.; Roesky, H. W.; Granitzka, M.; Stalke, D. J. Am. Chem. Soc. 2010, 132, 10018-10020
115. Shinohara, A.; McBee, J.; Waterman, R.; Tilley, T. D. Organometallics 2008, 27, 5717-5722
116. Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175-292
117. Corey, J. Y. Chem. Rev. 2011, 111, 863-1071
118. Bruker APEX2, SAINT, and SHELXTL; Bruker AXS Inc.: Madison, WI, 2009.
119. Sheldrick, G. M. SADABS; University of Göttingen, Göttingen, Germany, 2009.
120. Sheldrick, G. M. Acta Crystallogr. 2008, A 64, 112-122
121. Dittrich, B.; Hübschle, C. B.; Messerschmidt, M.; Kalinowski, R.; Girnt, D.; Luger, P. Acta Crystallogr. 2005, A 61, 314-320
122. Hansen, N. K.; Coppens, P. Acta Crystallogr. 1978, A 34, 909-921
123. Hübschle, C. B.; Luger, P.; Dittrich, B. J. Appl. Crystallogr. 2007, 40, 623-627
124. Koritsánszky, T.; Richter, T.; Macchi, P.; Volkov, A.; Gatti, C.; Howard, S.; Mallinson, P. R.; Farrugia, L.; Su, Z. W.; Hansen, N. K. Freie Universität Berlin, Berlin, 2003.
125. Dittrich, B.; Hübschle, C. B.; Luger, P.; Spackman, M. A. Acta Crystallogr. 2006, D65, 1325-1335
126. Rogers, R. D.; Atwood, J. L.; Foust, D.; Rausch, M. D. J. Cryst. Mol. Struct. 1981, 11, 183-188