Remarkable behavior of a bifunctional alkynylborane zirconocene complex toward donor ligands and acetylenes

Journal of the American Chemical Society

Volumn 135, Issue 46, 2013, Pages 17444-17456

  Kumar Podiyanachari, Santhosh ^a   Kehr, Gerald ^a   Mück Lichtenfeld, Christian ^a   Daniliuc, Constantin G ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON-CARBON COUPLING; FRUSTRATED LEWIS PAIRS; REACTION PATTERNS; REDUCTIVE COUPLINGS; REGIO-SELECTIVE; TERMINAL ALKYNE; TRIMETHYLSILYL; ZIRCONOCENE COMPLEXES;

ACETYLENE; ADDITION REACTIONS; CARBON; CARBON MONOXIDE; ORGANIC POLYMERS; X RAY DIFFRACTION; ZIRCONIUM;

LIGANDS;

ACETYLENE DERIVATIVE; BORANE DERIVATIVE; CARBON MONOXIDE; LEWIS ACID; LEWIS BASE; LIGAND; NITRILE; ZIRCONIUM; ZIRCONOCENE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CONFORMATION; CRYSTAL STRUCTURE; FLUORINE NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; ROOM TEMPERATURE; TEMPERATURE; X RAY DIFFRACTION;

EID: 84888342195     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja408385h     Document Type: Article

References (137)

1. Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 3623-3625
2. Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-10031
3. Bochmann, M.; Lancaster, S. J.; Hursthouse, M. B.; Abdul Malik, K. M. Organometallics 1994, 13, 2235-2243
4. Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170
5. Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128-6129
6. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434
7. Pindado, G. J.; Thornton-Pett, M.; Bouwkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem., Int. Ed. 1997, 36, 2358-2361
8. Corradi, M. M.; Pindado, J. G.; Sarsfield, M. J.; Thornton-Pett, M.; Bochmann, M. Organometallics 2000, 19, 1150-1159
9. Hill, M.; Kehr, G.; Erker, G.; Kataeva, O.; Fröhlich, R. Chem. Commun. 2004, 1020-1021
10. Tilley, T. D. Organometallics 1985, 4, 1452-1457
11. Binger, P.; Sandmeyer, F.; Krüger, C.; Erker, G. Tetrahedron 1995, 51, 4277-4290
12. Podiyanachari, S. K.; Fröhlich, R.; Daniliuc, C. G.; Petersen, J. L.; Christian, M.-L.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2012, 51, 8830-8833
13. Hill, M.; Erker, G.; Kehr, G.; Fröhlich, R.; Kataeva, O. J. Am. Chem. Soc. 2004, 126, 11046-11057
14. Emmert, M.; Kehr, G.; Fröhlich, R.; Erker, G. Chem.-Eur. J. 2009, 15, 8124-8127
15. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. 1976, 15, 333-340
16. Parks, D. J.; Spence, H.; von, R. E.; Piers, W. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 809-811
17. Spence, H.; von, R. E.; Parks, D. J.; Piers, W. E.; MacDonald, M.-A.; Zaworotko, M. J.; Rettig, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1230-1233
18. Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345-354
19. Spence, H.; von, R. E.; Piers, W. E.; Sun, Y.; Parvez, M.; MacGillivray, L. R.; Zaworotko, M. J. Organometallics 1998, 17, 2459-2469
20. Parks, D. J.; Piers, W. E.; Yap, G. P. A. Organometallics 1998, 17, 5492-5503
21. Rosenthal, U.; Ohff, A.; Michalik, M.; Görls, H.; Burlakov, V. V.; Shur, C, B. Angew. Chem., Int. Ed. 1993, 32, 1193-1195
22. Rosenthal, U.; Ohff, A.; Baumann, W.; Tillack, A. Z. Anorg. Allg. Chem. 1995, 621, 77-83
23. Bach, M. A.; Beweries, T.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A.; Rosenthal, U. Organometallics 2007, 26, 4592-4597
24. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1755-1757
25. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165-11173
26. Dahlmann, M.; Erker, G.; Fröhlich, R.; Meyer, O. Organometallics 2000, 19, 2956-2967
27. Kleigrewe, N.; Brackemeyer, T.; Kehr, G.; Fröhlich, R.; Erker, G. Organometallics 2001, 20, 1952-1955
28. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
29. Frustrated Lewis Pairs I, Uncovering and Understanding; Erker, G.; Stephan, D. W., Eds.; Topics in Current Chemistry; Springer: Heidelberg, New York, Dordrecht, London, 2013, Vol. 332.
30. Frustrated Lewis Pairs II, Expanding the Scope; Erker, G.; Stephan, D. W., Eds.; Topics in Current Chemistry; Springer: Heidelberg, New York, Dordrecht, London, 2013; Vol. 334.
31. Rosorius, C.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G. Organometallics 2011, 30, 4211-4219
32. Stute, A.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Commun. 2011, 47, 4288-4290
33. Chapman, A. M.; Haddow, M. F.; Wass, D. F. J. Am. Chem. Soc. 2011, 133, 8826-8829
34. Chapman, A. M.; Haddow, M. F.; Wass, D. F. J. Am. Chem. Soc. 2011, 133, 18463-18478
35. Chapman, A. M.; Wass, D. F. Dalton Trans. 2012, 9067-9072
36. Xu, X.; Kehr, G.; Daniliuc, C. G.; Erker, G. J. Am. Chem. Soc. 2013, 135, 6465-6476
37. Frömel, S.; Kehr, G.; Fröhlich, R.; Daniliuc, C. G.; Erker, G. Dalton Trans. 2013, 42, 14531-14536
38. Petersen, J. L.; Dahl, L. F. J. Am. Chem. Soc. 1975, 97, 6416-6422
39. Petersen, J. L.; Dahl, L. F. J. Am. Chem. Soc. 1975, 97, 6422-6433
40. Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729-1742
41. Green, J. C. Chem. Soc. Rev. 1998, 27, 263-271
42. Fachinetti, G.; Floriani, C.; Marchetti, F.; Mellini, M. J. Chem. Soc., Dalton Trans. 1978, 1398-1403
43. Erker, G.; Dorf, U.; Kruger, C.; Angermund, K. J. Organomet. Chem. 1986, 301, 299-312
44. Atwood, J. L.; Rogers, R. D.; Hunter, W. E.; Floriani, C.; Fachinetti, G.; Chiesi-Villa, A. Inorg. Chem. 1980, 19, 3812-3817
45. Guo, Z.; Swenson, D. C.; Guram, A. S.; Jordan, R. F. Organometallics 1994, 13, 766-773 and references cited in these papers
46. TURBOMOLE V6.3 2011, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007; available from http://www.turbomole.com.
47. Numerical calculation of vibrational normal modes with SNF: Neugebauer, J.; Reiher, M.; Kind, C.; Hess, B. A. J. Comput. Chem. 2002, 23, 895-910
48. TPSS functional: Tao, J.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 91, 146401-146404
49. def2-TZVP basis set: Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
50. D3 dispersion correction: Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104-15419
51. D3-BJ damping function: Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456-1465
52. Sikora, D. J.; Rausch, M. D.; Rogers, R. D.; Atwood, J. L. J. Am. Chem. Soc. 1981, 103, 1265-1267
53. Rausch, M. D.; Moriarty, K. J.; Atwood, J. L.; Hunter, W. E.; Samuel, E. J. Organomet. Chem. 1987, 327, 39-54
54. Guo, Z.; Swenson, D. C.; Guram, A. S.; Jordan, R. F. Organometallics 1994, 13, 766-773
55. Choukroun, R.; Lorber, C.; Lepetit, C.; Donnadieu, B. Organometallics 2003, 22, 1995-1997
56. Shen, H.; Jordan, R. J. Organometallics 2003, 22, 2080-2086
57. Bradley, C. A.; Flores-Torres, S.; Lobkovsky, E.; Abruña, H. D.; Chirik, P. J. Organometallics 2004, 23, 5332-5346
58. Zachmanoglou, C. E.; Melnick, J. G.; Bridgewater, B. M.; Churchill, D. G.; Parkin, G. Organometallics 2005, 24, 603-611
59. Bazinet, P.; Tilley, T. D. Organometallics 2008, 27, 1267-1274
60. Casper, D. J.; Sklyarov, A. V.; Hardcastle, S.; Barr, T. L.; Försterling, H. F.; Surerus, K. F.; Hossain, M. M. Inorg. Chim. Acta 2006, 359, 3129-3138
61. Wu, J.; Sharp, P. R. Organometallics 2008, 27, 4810-4816
62. Miller, A. J. M.; Labinger, J. A.; Bercaw, J. E. Organometallics 2010, 29, 4499-4516
63. McGovern, G. P.; Hung-Low, F.; Tye, J. W.; Bradley, C. A. Organometallics 2012, 31, 3865-3879
64. Hurlburt, P. K.; Rack, J. J.; Luck, J. S.; Dec, S. F.; Webb, J. D.; Anderson, O. P.; Strauss, S. H. J. Am. Chem. Soc. 1994, 116, 10003-10014
65. Goldman, A. S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1996, 118, 12159-12166
66. Lupinetti, A. J.; Frenking, G.; Strauss, S. H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2113-2116
67. Ricks, A. M.; Gagliardi, L.; Duncan, M. A. J. Am. Chem. Soc. 2010, 132, 15905-15907
68. La Pierre, H. S.; Arnold, J.; Bergman, R. G.; Toste, F. D. Inorg. Chem. 2012, 21, 13334-13344
69. Brathwaite, A. D.; Duncan, M. A. J. Phys. Chem. A. 2013, 10.1021/jp400793h
70. See also: Lupinetti, A. J.; Strauss, S. H.; Frenking, G. Nonclassical Metal Carbonyls. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2007, Vol. 49, 1-112.
71. Burg, A. B.; Schlesinger, H. I. J. Am. Chem. Soc. 1937, 59, 780-787
72. Cowan, R. D. J. Chem. Phys. 1950, 18, 1101-1107
73. Bethke, G. W.; Wilson, M. K. J. Chem. Phys. 1957, 26, 1118-1130
74. Finze, M.; Bernhardt, E.; Terheiden, A.; Berkei, M.; Willner, H.; Christen, D.; Oberhammer, H.; Aubke, F. J. Am. Chem. Soc. 2002, 124, 15385-15398
75. Jordan, R. F.; Bajgur, C. S.; Willett, R.; Scott, B. J. Am. Chem. Soc. 1986, 108, 7410-7411
76. Bradley, C. A.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2003, 125, 8110-8111
77. Bartlett, R. A.; Power, P. P. Organometallics 1986, 5, 1916-1917
78. Olmstead, M. M.; Power, P. P.; Weese, K. J.; Doedens, R. J. J. Am. Chem. Soc. 1987, 109, 2541-2542
79. Pilz, M.; Allwohn, J.; Hunold, R.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1370-1372
80. Pilz, M.; Allwohn, J.; Willershausen, P.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. Engl. 1990, 29, 1030-1032
81. Sahin, Y.; Hartmann, M.; Geiseler, G.; Schweikart, D.; Balzereit, C.; Frenking, G.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. 2001, 40, 2662-2665
82. Chiu, C.-W.; Gabbaï, F. P. Angew. Chem., Int. Ed. 2007, 46, 6878-6881
83. Yu, J.; Kehr, G.; Daniliuc, C. G.; Erker, G. Eur. J. Inorg. Chem. 2013, 19, 3312-3315
84. Möbus, J.; Kehr, G.; Daniliuc, C. G.; Fröhlich, R.; Erker, G. Dalton Trans. 2013, 10.1039/c3dt52373j
85. Eisch, J. J. Adv. Organomet. Chem. 1996, 39, 355-391
86. Power, P. P. Chem. Rev. 1999, 99, 3463-3503
87. Fischer, R. C.; Power, P. P. Chem. Rev. 2010, 110, 3877-3923
88. Zweifel, G.; Arzoumanian, H. Tetrahedron Lett. 1966, 7, 2535-2538
89. Kow, R.; Rathke, M. W. J. Am. Chem. Soc. 1973, 95, 2715-2716
90. Pelter, A.; Bugden, G.; Rosser, R. Tetrahedron Lett. 1985, 26, 5097-5100
91. Tomioka, T.; Sankranti, R.; Vaughan, T. G.; Maejima, T.; Yanase, T. J. Org. Chem. 2011, 76, 8053-8058
92. Tomioka, T.; Takahashi, Y.; Maejima, T. Org. Biomol. Chem. 2012, 10, 5113-5118
93. Jäger, H.; Hesse, G. Chem. Ber. 1962, 95, 345-349
94. Haag, A.; Hesse, G. Justus Liebigs Ann. Chem. 1971, 751, 95-108
95. Mömming, C. M.; Frömel, S.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G. J. Am. Chem. Soc. 2009, 131, 12280-12289
96. Menard, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 8272-8275
97. Erker, G. Pure Appl. Chem. 2012, 84, 2203-2217
98. Menard, G.; Tran, L.; McCahill, J. S. J.; Lough, A. J.; Stephan, D. W. Organometallics 2013, 10.1021/om400222w
99. Erker, G.; Zwettler, R.; Krüger, C.; Schlund, R.; Hyla-Kryspin, I.; Gleiter, R. J. Organomet. Chem. 1988, 346, C15-C18
100. Erker, G.; Schlund, R.; Krüger, C. Organometallics 1989, 8, 2349-2355
101. Hyla-Kryspin, I.; Gleiter, R.; Krüger, C.; Zwettler, R.; Erker, G. Organometallics 1990, 9, 517-523
102. Erker, G.; Zwettler, R.; Krüger, C.; Hyla-Kryspin, I.; Gleiter, R. Organometallics 1990, 9, 524-530
103. Mömming, C. M.; Kehr, G.; Wibbeling, B.; Fröhlich, R.; Schirmer, B.; Grimme, S.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 2414-2417
104. Feldhaus, P.; Schirmer, B.; Wibbeling, B.; Daniliuc, C. G.; Fröhlich, R.; Grimme, S.; Kehr, G.; Erker, G. Dalton Trans. 2012, 41, 9135-9142
105. See for a comparison: Xu, B.-H.; Kehr, G.; Fröhlich, R.; Wibbeling, B.; Schirmer, B.; Grimme, S.; Erker, G. Angew. Chem., Int. Ed. 2011, 50, 7183-7186
106. Werner, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 927-949
107. Werner, H. Comments Inorg. Chem. 1990, 10, 267-295
108. Bender, G.; Kehr, G.; Fröhlich, R.; Petersen, J. L.; Erker, G. Chem. Sci. 2012, 3, 3534-3540
109. Bender, G.; Kehr, G.; Daniliuc, C. G.; Dao, Q. M.; Ehrlich, S.; Grimme, S.; Erker, G. Chem. Commun. 2012, 48, 11085-11087
110. Rosenthal, U.; Arndt, P.; Baumann, W.; Burlakov, V. V.; Spannenberg, A. J. Organomet. Chem. 2003, 670, 84-96
111. Rosenthal, U.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A. Eur. J. Inorg. Chem. 2004, 22, 4739-4750
112. Rosenthal, U. Angew. Chem., Int. Ed. 2004, 43, 3882-3887
113. Rosenthal, U.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A. Organometallics 2005, 24, 456-471
114. Rosenthal, U.; Burlakov, V. V.; Bach, M. A.; Beweries, T. Chem. Soc. Rev. 2007, 36, 719-728
115. Suzuki, N.; Nishiura, M.; Wakatsuki, Y. Science 2002, 295, 660-663
116. Suzuki, N.; Aihara, N.; Takahara, H.; Watanabe, T.; Iwasaki, M.; Saburi, M.; Hashizume, D.; Chihara, T. J. Am. Chem. Soc. 2004, 126, 60-61
117. Ugolotti, J.; Dierker, G.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 2622-2625
118. Ugolotti, J.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G. J. Am. Chem. Soc. 2009, 131, 1996-2007
119. Suzuki, N.; Hashizume, D.; Koshino, H.; Chihara, T. Angew. Chem., Int. Ed. 2008, 47, 5198-5202
120. Xi, Z.; Fischer, R.; Hara, R.; Sun, W.-H.; Obora, Y.; Suzuki, N.; Nakajima, K.; Takahashi, T. J. Am. Chem. Soc. 1997, 119, 12842-12848
121. Suzuki, N.; Shimura, T.; Sakaguchi, Y.; Masuyama, Y. Pure Appl. Chem. 2011, 83, 1781-1788
122. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829-2832
123. Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310-2312
124. Fagan, P. J.; Burns, E. G.; Calabrese, J. C. J. Am. Chem. Soc. 1988, 110, 2979-2981
125. Swanson, D. R.; Negishi, E. Organometallics 1991, 10, 825-826
126. Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880-1889
127. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124-1126
128. Welch, G. C.; Stephan, D. W. J. Am. Chem. Soc. 2007, 129, 1880-1881
129. Spies, P.; Erker, G.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem. Commun. 2007, 5072-5074
130. Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 7543-7546
131. Stephan, D. W.; Erker, G. Top. Curr. Chem. 2013, 332, 85-110
132. Hooft, R. W. W. Bruker AXS, 2008, Delft, The Netherlands.
133. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326
134. Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr. 2003, A59, 228-234
135. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473
136. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
137. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13