Transition-metal-promoted or -catalyzed exocyclic alkyne insertion via zirconacyclopentene with carborane auxiliary: Formation of symmetric or unsymmetric benzocarboranes

Journal of the American Chemical Society

Volumn 134, Issue 6, 2012, Pages 3242-3254

  Ren, Shikuo ^a   Qiu, Zaozao ^a   Xie, Zuowei ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED ALKYNES; ALKYNE INSERTIONS; CARBORANES; CATALYTIC AMOUNTS; CATALYTIC REACTIONS; INSERTION PRODUCTS; NICKEL COMPLEX; ONE POT; REACTION MECHANISM; STRUCTURAL CHARACTERIZATION; THREE-COMPONENT; TRIMERIZATION;

CATALYSIS; IRON COMPOUNDS; NICKEL; REACTION INTERMEDIATES; ZIRCONIUM; ZIRCONIUM COMPOUNDS;

ACETYLENE;

ALKYNE DERIVATIVE; CARBORANE DERIVATIVE; CYCLOPENTENE DERIVATIVE; FERRIC CHLORIDE; LITHIUM DERIVATIVE; NICKEL CHLORIDE; NICKEL COMPLEX; TRANSITION ELEMENT; ZIRCONIUM DERIVATIVE; ZIRCONOCENE;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; ISOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84856832752     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211485t     Document Type: Article

References (107)

1. Roberts, J. D.; Simmons, H. E., Jr.; Carlsmith, L. A.; Vaughan, C. W. J. Am. Chem. Soc. 1953, 75, 3290-3291
2. Hart, H. In Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S., Ed.; Wiley: Chichester, U.K., 1994; Chapter 18, pp 1017-1134.
3. Hoffmann, R. W. In Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
4. Gilchrist, T. L. In Chemistry of Functional Groups, Supplement C; Patai, S.; Rappoport, Z., Eds.; Wiley, Chichester, U.K., 1983; Chapter 11, pp 383-419.
5. Jones, W. M.; Klosin, J. Adv. Organomet. Chem. 1998, 42, 147-221
6. Schore, N. E. Chem. Rev. 1988, 88, 1081-1119
7. Trost, B. M. Science 1991, 254, 1471-1477
8. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92
9. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915
10. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198
11. Schmid, R.; Kirchner, K. Eur. J. Inorg. Chem. 2004, 2609-2626
12. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346-1416
13. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780-1824
14. Kotha, S.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741-4767
15. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915
16. Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307-2327
17. Tanaka, K. Synlett 2007, 10, 1977-1993
18. Shibata, T.; Tsuchikama, K. Org. Biomol. Chem. 2008, 6, 1317-1323
19. Yamamoto, Y. Curr. Org. Chem. 2005, 9, 503-519
20. Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085-1094
21. Varela, J. A.; Saá, C. Chem. Rev. 2003, 103, 3787-3801
22. Henry, G. D. Tetrahedron 2004, 60, 6043-6061
23. Agenet, N.; Busine, O.; Slowinski, F.; Gandon, V.; Aubert, C.; Malacria, M. Org. React. 2007, 68, 1-302
24. Galan, B. R.; Rovis, T. Angew. Chem., Int. Ed. 2009, 48, 2830-2834
25. Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2011, 40, 3430-3444
26. Sakiyama, N.; Hojo, D.; Noguchi, K.; Tanaka, K. Chem.-Eur. J. 2011, 17, 1428-1432
27. Qiu, Z.; Xie, Z. Angew. Chem., Int. Ed. 2009, 48, 5729-5732
28. Sugiyama, Y.; Kato, R.; Sakurada, T.; Okamoto, S. J. Am. Chem. Soc. 2011, 133, 9712-9715
29. Kawatsura, M.; Yamamoto, M.; Namioka, J.; Kajita, K.; Hirakawa, T.; Itoh, T. Org. Lett. 2011, 13, 1001-1003
30. Songis, O.; Míšek, J.; Schmid, M. B.; Kollá rovič, A.; Stará, I. G.; Saman, D.; Císařová, I.; Starý, I. J. Org. Chem. 2010, 75, 6889-6899
31. Watanabe, J.-I.; Sugiyama, Y.-K.; Nomura, A.; Azumatei, S.; Goswami, A.; Saino, N.; Okamoto, S. Macromolecules 2010, 43, 2213-2218
32. Dachs, A.; Torrent, A.; Roglans, A.; Parella, T.; Osuna, S.; Solà, M. Chem.-Eur. J. 2009, 15, 5289-5300
33. Hsieh, J.-C.; Cheng, C.-H. Chem. Commun. 2008, 2992-2994
34. Míšek, J.; Teplý, F.; Stará, I. G.; Tichý, M.; Šaman, D.; Císařová, I.; Vojtíšek, P.; Starý, I. Angew. Chem., Int. Ed. 2008, 47, 3188-3191
35. Onodera, G.; Matsuzawa, M.; Aizawa, T.; Kitahara, T.; Shimizu, Y.; Kezuka, S.; Takeuchi, R. Synlett 2008, 755-758
36. Tanaka, K.; Sagae, H.; Toyoda, K.; Noguchi, K.; Hirano, M. J. Am. Chem. Soc. 2007, 129, 1522-1523
37. Heller, B.; Gutnov, A.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Redkin, D.; Sundermann, C.; Sundermann, B. Chem.-Eur. J. 2007, 13, 1117-1128
38. Yamamoto, Y.; Ishii, J.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2004, 126, 3712-3713
39. Yamamoto, Y.; Ishii, J.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 9625-9631
40. Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
41. Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448
42. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336-3346
43. Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874
44. RajanBabu, T. V.; Nugent, W. A.; Taber, D. F.; Fagan, P. J. J. Am. Chem. Soc. 1988, 110, 7128-7135
45. Dufková, L.; Kotora, M.; Císařová, I. Eur. J. Org. Chem. 2005, 2491-2499
46. Takahashi, T.; Tsai, F.-Y.; Li, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1999, 121, 11093-11100
47. Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672-1680
48. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361-362
49. Qiu, Z.; Ren, S.; Xie, Z. Acc. Chem. Res. 2011, 44, 299-309
50. Qiu, Z.; Xie, Z. Sci. China, Ser. B: Chem. 2009, 52, 1544-1558
51. Deng, L.; Chan, H.-S.; Xie, Z. J. Am. Chem. Soc. 2006, 128, 7728-7729
52. Qiu, Z.; Wang, S. R.; Xie, Z. Angew. Chem., Int. Ed. 2010, 49, 4649-4652
53. Qiu, Z.; Xie, Z. J. Am. Chem. Soc. 2010, 132, 16085-16093
54. Qiu, Z.; Xie, Z. J. Am. Chem. Soc. 2009, 131, 2084-2085
55. Ren, S.; Qiu, Z.; Xie, Z. Angew. Chem., Int. Ed. 2012, 51, 1010-1013
56. Ren, S.; Chan, H.-S.; Xie, Z. Organometallics 2009, 28, 4106-4114
57. Ren, S.; Chan, H.-S.; Xie, Z. J. Am. Chem. Soc. 2009, 131, 3862-3863
58. This work is a part of Shikuo Rens Ph.D. thesis. See: Ren, S. Ph.D. Thesis, The Chinese University of Hong Kong, April 2010.
59. Bennett, M. A.; Macgregor, S. A.; Wenger, E. Helv. Chim. Acta 2001, 84, 3084-3104
60. Deng, L.; Chan, H.-S.; Xie, Z. J. Am. Chem. Soc. 2005, 127, 13774-13775
61. Diaz, M.; Jaballas, J.; Arias, J.; Lee, H.; Onak, T. J. Am. Chem. Soc. 1996, 118, 4405-4410
62. Ren, S.; Deng, L.; Chan, H.-S.; Xie, Z. Organometallics 2009, 28, 5749-5756
63. Takahashi, T. Pure Appl. Chem. 2001, 73, 271-274
64. Xi, Z.; Li, Z. Top. Organomet. Chem. 2004, 8, 27-56
65. Chen, C.; Xi, C. Chin. Sci. Bull. 2010, 55, 3235-3247
66. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N.; Nakajima, K. Organometallics 1994, 13, 4183-4185
67. Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154-5155
68. Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102
69. Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355-8358
70. Takahashi, T.; Sun, W.-H.; Liu, Y.; Nakajima, K.; Kotora, M. Organometallics 1998, 17, 3841-3843
71. Ura, Y.; Li, Y.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1998, 39, 2787-2790
72. Kotora, M.; Xi, C.; Takahashi, T. Tetrahedron Lett. 1998, 39, 4321-4324
73. Kotora, M.; Noguchi, Y.; Takahashi, T. Collect. Czech. Chem. Commun. 1999, 64, 1119-1124
74. Takahashi, T.; Sun, W.-H.; Nakajima, K. Chem. Commun. 1999, 1595-1596
75. Yamamoto, Y.; Ohno, T.; Itoh, K. Chem. Commun. 1999, 1543-1544
76. Takahashi, T.; Huo, S. Q.; Hara, R.; Noguchi, Y.; Nakajima, K.; Sun, W.-H. J. Am. Chem. Soc. 1999, 121, 1094-1095
77. Duan, Z.; Sun, W.-H.; Liu, Y.; Takahashi, T. Tetrahedron Lett. 2000, 41, 7471-7474
78. Ura, Y.; Li, Y.; Tsai, F.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189
79. Takahashi, T.; Sun, W.-H.; Duan, Z.; Shen, B. Org. Lett. 2000, 2, 1197-1199
80. Xi, C.; Kotora, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2000, 65, 945-950
81. Xi, Z.; Li, P. Angew. Chem., Int. Ed. 2000, 39, 2950-2952
82. Li, Y.; Ura, Y.; Tsai, F. Y.; Xu, F.; Takahashi, T. Heterocycles 2001, 54, 943-955
83. Takahashi, T.; Li, Y.; Ito, T.; Xu, F.; Nakajima, K.; Liu, Y. J. Am. Chem. Soc. 2002, 124, 1144-1145
84. Wang, H.; Tsai, F.-Y.; Nakajima, K.; Takahashi, T. Chem. Lett. 2002, 31, 578-579
85. Zhao, C.; Li, P.; Cao, X.; Xi, Z. Chem.-Eur. J. 2002, 8, 4292-4298
86. Chen, C.; Xi, C.; Ai, Z.; Hong, X. Org. Lett. 2006, 8, 4055-4058
87. Duan, Z.; Nakajim, K.; Takahashi, T. Chem. Commun. 2001, 1672-1673
88. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183-4185
89. 2+ = 0.771 V. See: Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Principles of Structure and Reactivity, 4 th ed.; Harper Collins: New York, 1993.
90. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293-1314
91. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217-6254
92. Russell, S. K.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2011, 133, 8858-8861
93. Wang, C.; Li, X.; Wu, F.; Wan, B. Angew. Chem., Int. Ed. 2011, 50, 7162-7166
94. DSouza, B. R.; Lane, T. K.; Louie, J. Org. Lett. 2011, 13, 2936-2939
95. Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925-2928
96. Moreau, B.; Wu, J. Y.; Ritter, T. Org. Lett. 2009, 11, 337-339
97. Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858-5859
98. Fürstner, A.; Majima, K.; Martín, R.; Krause, H.; Kattnig, E.; Goddard, R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 1992-2004
99. Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844-9845
100. McLaughlin, E. C.; Doyle, M. P. J. Org. Chem. 2008, 73, 4317-4319
101. Bieber, L. W.; Silva, M. F. Tetrahedron Lett. 2004, 45, 8281-8283
102. Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412-420
103. Bieber, L. W.; Silva, M. F. Tetrahedron Lett. 2007, 48, 7088-7090
104. Bestmann, H. J.; Zeibig, T.; Vostrowsky, O. Synthesis 1990, 1039-1047
105. Page, P. C. B.; Rosenthal, S. Tetrahedron 1990, 46, 2573-2586
106. Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1996.
107. Sheldrick, G. M. SHELXTL: Structure Determination Software Programs, version 5.10 for Windows NT; Bruker Analytical X-ray Systems, Inc.: Madison, WI, 1997.