Chinese Journal of Organic Chemistry >
Progresses on Synthesis and Applications of Bis(cyclopentadieny)titanacycles
Received date: 2013-10-10
Revised date: 2013-12-30
Online published: 2014-01-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 20972037), the Special Funds for Key Innovation Team of Zhejiang Province (No. 2010R50017), the Excellent Young Teacher Support Program of Hangzhou Normal University (No. 2011-01-013) and the Program for Changjiang Scholars and Innovative Research Team in Chinese University (No. IRT 1231).
Titanacycles, containing two carbon metal bonds in the molecule, have emerged as a series of significant intermediates in organic synthesis. The structural characteristics, preparation and synthetic applications of bis(cyclopentadienyl)titana-three, four, five, or six-membered rings have been summarized in the present review, in which the selective cleavage and reactivity of C—Ti bond in the titanacyle have been discussed.
Wang Ping , Zhang Yanjing , Wang Wei , Zheng Weixin . Progresses on Synthesis and Applications of Bis(cyclopentadieny)titanacycles[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 865 -875 . DOI: 10.6023/cjoc201310007
[1] (a) Pramod, R. C.; Janis, L. Adv. Synth. Catal. 2006, 348, 2307.
(b) Jesu′s, A. V.; Carlos, S. Chem. Rev. 2003, 103, 3787.
(c) Shinichi, S.; Yoshinori, Y. Chem. Rev. 2000, 100, 2901.
(d) Iwao, O.; Maria, T.; Li, Z. Y.; Robert, J. D. Chem. Rev. 1996, 96, 635.
(e) Itaru, N.; Yoshinori, Y. Chem. Rev. 2004, 104, 2127.
(f) Zhang, C. H.; Zhang, H.; Wei, A. L.; He, X. M. Acta Chim. Sinica 2013, 71, 1373 (in Chinese).
(张春红, 张弘, 魏爱琳, 何旭敏, 夏海平, 化学学报, 2013, 71, 1373.)
[2] (a) Gerald, D. Angew. Chem., Int. Ed. 1999, 38, 1699.
(b) Shinich, I. Organomet. News 2007, 1, 2.
(c) Kochi, J. K. ACS Symposium Series, Vol. 55, Oxford University Press, New York, 1977, p. 167.
[3] (a) Tarselli, M. A. Nat. Chem. 2013, 5, 546.
(b) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
(c) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
[4] (a) Dunitz, J. D.; Orgel, L. E. Nature 1953, 171, 121.
(b) Dunitz, J. D.; Orgel, L. E. J. Chem. Phys. 1955, 23, 954.
[5] Piotr, S.; Anna, D. J.; Jozef, U.; Lucjan, B. J. Organometallics 2011, 30, 1741.
[6] Xi, Z. F.; Li, Z. P. Top. Organomet. Chem. 2004, 8, 27.
[7] Rosebthal, U.; Vladimir, V. B. In Titanium and Zirconium in Organic Synethesis, Ed.: Marek, I., Wiley-VCH, 2002, p. 355.
[8] Fischer, A. K.; Wilkinson, G. J. Inorg. Nucl. Chem. 1956, 2, 149.
[9] Chirik, P. J. Organometallics 2010, 29, 1500.
[10] Eisch, J. J.; Adeosun, A. A.; Birmingham, J. M. Eur. J. Inorg. Chem. 2007, 1, 39.
[11] Watt, G. W.; Drummond, F. O. J. Am. Chem. Soc. 1970, 92, 826.
[12] Freitag, M. A.; Gordon, M. S. J. Phys. Chem. A 2002, 106, 7921.
[13] (a) Liu, C. F.; Chen, J. H.; Chen, S. C.; Chen, K. Y.; Lee, G. H.; Peng, S. M. J. Org. Chem. 2005, 690, 291.
(b) Timothy, J. C.; Christopher, A. R.; Ian, M. J. Am. Chem. Soc. 2006, 128, 9582.
[14] (a) Xu, S.; Tao, X-C. Acta Chim. Sinica 2004, 24, 250 (in Chinese).
(许胜, 陶晓春, 化学学报, 2004, 24, 250.)
(b) Fumie, S.; Hiroaki, I.; Masao, S. Tetrahedron Lett.1981, 22, 85.
[15] (a) Bonnemann, O. Angew. Chem., Int. Ed. Engl. 1985, 24, 248.
(b) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
(c) Takeda, T.; Tsubouchi, A. J. Synth. Org. Chem. 2008, 66, 1178.
[16] Li, Z. P.; Zhao, P. J.; Xi, Z. F. Chemistry 2002, (2), 78 (in Chinese).
(李志平, 赵炳筠, 席振峰, 化学通报, 2002, (2), 78.)
[17] (a) Negishi, E.; Huo, S. Q. In Titanium and Zirconium in Organic Synethesis, Ed.: Marek, I., Wiely-VCH, 2002, p. 1.
(b) Takahashi, T.; Li, Y. Z. In Titanium and Zirconium in Organic Synethesis, Ed.: Marek, I., Wiely-VCH, 2002, p. 50.
[18] (a) Takahashi, T.; Murakami, M.; Kunishige, M.; Saburi, M.; Uchida, Y.; Kozawa, K.; Uchida, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1989, 5, 761.
(b) Takahashi, T.; Takashi, S.; Nitto, Y.; Masahiko, S.; Christophe, J. R.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266.
(c) Takahashi, T.; Suzuki, N.; Kageyama, M.; Nitto, Y.; Saburi, M.; Negishi, E. Chem. Lett. 1991, 9, 1579.
(d) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687.
(e) Takahashi, T.; Xi, C. J.; Xi, Z. F.; Kageyama, M.; Fischer, R.; Nakajima, K.; Negishi, E. J. Org. Chem. 1998, 63, 6802.
[19] Negishi, E.; Takahashi, T. Synthesis 1988, 1.
[20] Negishi, E.; Fredrik, E. C.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
[21] (a) Nicolas, M.; Narcis, A.; Didier, B.; Francois, M.; Pascal, L. F. Organometallics 1998, 17, 2677.
(b) Shur, V. B.; Berkovich, E. G.; Volpin, M. E. J. Organomet. Chem. 1982, 228, 36.
(c) Shur, V. B.; Burlakov, V. V.; Volpin, M. E. J. Organomet. Chem. 1988, 347, 77.
(d) Fumie, S.; Hirokazu, U. In Titanium and Zirconium in Organic Synethesis, Ed.: Marek, I., Wiely-VCH, 2002, p. 319.
[22] Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310.
[23] (a) Uwe, R.; Vladimir, V. B.; Marc, A. B.; Torsten, B. Chem. Soc. Rev. 2007, 36, 719.
(b) Uwe, R.; Vladimir, V. B.; Perdita, A.; Wolfgang, B.; Anke, S. Organometallics 2005, 24, 456.
[24] Kaleta, K.; Ruhmann, M.; Theilmann, O.; Beweries, T.; Roy, S.; Arndt, P.; Villinger, A.; Eluvathingal, D. J.; Schulz, A.; Rosenthal, U. J. Am. Chem. Soc. 2011, 133, 5463.
[25] (a) Leigh, G. Chem. Eur. J. 1997, 3, 332.
(b) Uwe, R.; Vladimir, V.; Burlakov, P. A.; Wolfgang, B.; Anke, S. Organometallics 2003, 22, 884.
[26] Martin, L.; Anke, S.; Wolfgang, B.; Jiao, H. J.; Christine, F.; Sven, H.; Perdita, A.; Uwe, R. J. Am. Chem. Soc. 2010, 132, 43690.
[27] (a) Uwe, R.; Vladimir, V. B. In Titanium and Zirconium in Organic Synethesis, Ed.: Marek, I., Wiely-VCH, 2002, p. 355.
(b) Bradford, C.; Wagenen, V.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495.
[28] Lefeber, C.; Ohff, A.; Tillack, A.; Baumann, W.; Kempe, R.; Burlakov, V. V.; Rosenthal, U.; Görls, H. J. Organomet. Chem. 1995, 501, 179.
[29] Thomas, D.; Peulecke, N.; Burlakov, V. V.; Heller, B.; Baumann, W.; Spannenberg, A.; Kempe, R.; Rosenthal, U.; Beckhaus, R. Z. Anorg. Allg. Chem. 1998, 624, 919.
[30] Roy, S.; Jemmis, E. D.; Schulz, A; Beweries, T.; Rosenthal, U. Angew. Chem., Int. Ed. 2012, 51, 5347.
[31] (a) Rosenthal, U.; Burlakov, V. V.; Bach, M. A.; Beweries, T. Chem. Soc. Rev. 2007, 36, 719.
(b) Lamac, M.; Spannenberg, A.; Jiao, H.; Hansen, S.; Baumann, W.; Arndt, P.; Rosenthal, U. Angew. Chem., Int. Ed. 2010, 49, 2973.
(c) Becker, L.; Burlakov, V. V.; Arndt, P.; Spannenberg, A.; Baumann, W.; Jiao, H. J.; Rosenthal, U. Chem.-Eur. J. 2013, 19, 4230.
(d) Oishi, S.; Tsubouchi, A.; Takeda, T. J. Organomet. Chem. 2012, 696, 581.
[32] (a) Takeda, T. Bull. Chem. Soc. Jpn. 2005, 78, 195.
(b) Bernhard, B. Angew. Chem., Int. Ed. Engl. 1998, 37, 453.
[33] Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
[34] (a) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
(b) Petasis, N. A.; Lu, S.P.; Bzowej, E. I.; Fu, D.K.; Staszewski, J. P.; Akritopoulou-Zanze, I.; Patane, M. A.; Hu, Y. H. Pure Appl. Chem. 1996, 68, 667.
(c) Vaxelaire, C. Synlett 2009, 3221.
(d) Wu, K.; Mercado, E. V.; Pettus, T. R. R. J. Am. Chem. Soc. 2011, 133, 6114.
[35] Theilmann, O.; Ruhmann, M.; Villinger, A.; Schulz, A.; Wolfram, W. S. Angew. Chem., Int. Ed. 2010, 49, 9282.
[36] Beckhaus, R.; Santamaria, C. J. Organomet. Chem. 2001, 617, 81.
[37] Takeda, T. Chem. Rec. 2007, 7, 24.
[38] (a) Tebbe, F. N.; Parshall, G. W.; Ovenall, D. W. J. Am. Chem. Soc. 1979, 101, 5074.
(b) Howard, T. R.; Lee, J. B.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 6876.
(c) Lee, J. B.; Kevin, C. O.; Grubbs, R. H. J. Am. Chem. Soc. 1982, 104, 7491.
[39] John, R. S.; Bernard, D. S.; Robert, H. G. J. Org. Chem. 1990, 55, 843.
[40] Takahashi, T. In Titanium and Zirconium in Organic Synethesis, Ed.: Marek, I., Wiely-VCH, 2002, p. 475.
[41] (a) Gilliom, L. R.; Grubbs, R. H. Organometallics 1986, 5, 721.
(b) Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855.
[42] (a) Hawkins, J. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 2821.
(b) Beckhaus, R.; Wagner, T. J. Organomet. Chem. 1993, 460, 181.
(c) Stephen, L. B.; Robert, H. G. J. Am. Chem. Soc.1983, 105, 5490.
[43] (a) Kenneth, M. D.; Jerrick, J. J. J.; Kenneth, Z.; Gregory, N. J. Am. Chem. Soc. 1994, 116, 2147.
(b) Petasis, N. A.; Fu, D. K. Organometallics 1993, 12, 3776.
[44] Meinhart, J. D.; Grubbs, R. H. Bull. Chem. Soc. Jpn. 1988, 61, 171.
[45] Kenneth, M. D.; John, K. M. M. Tetrahedron Lett. 1991, 32, 1687.
[46] Shono, T.; Nagasawa, T.; Tsubouchi, A.; Takeda, T. Tetrahedron Lett. 2007, 48, 3521.
[47] Shono, T.; Nagasawa, T.; Tsubouchi, A.; Noguchi, K.; Takeda, T. Chem. Commun. 2008, 3537.
[48] Shono, T.; Kurashige, R.; Mukaiyama, R.; Tsubouchi, A.; Takeda, T. Chem. Eur. J. 2007, 13, 4074.
[49] Yatsumonji, Y.; Atake, Y.; Tsubouchi, A.; Takeda, T. Chem. Commun. 2009, 3375.
[50] (a) Fumie, S.; Hirokazu, U.; Sentaro, O. Chem. Rev. 2000, 100, 2835.
(b) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124.
[51] McDermott, J. X.; Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6529.
[52] (a) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687.
(b) Takahashi, T.; Xi, Z. F.; Nishihara, Y.; Huo, S.; Kasai, K.; Aoyagi, K.; Denisov, V.; Negishi, E. Tetrahedron 1997, 53, 912.
[53] Kimihiko, S.; Yasushi, N.; Huo, S. Q.; Xi, Z. F.; Takahashi, T. J. Organomet. Chem. 2001, 633, 18.
[54] Zhao, Z. B.; Ding, Y.; Zhao, G. J. Org. Chem. 1998, 63, 9285.
[55] Frederick, A. H.; Natasha, M. K.; Buchwald, L. S. J. Am. Chem. Soc. 1999, 121, 5881.
[56] (a) Zhao, C.; Yu, T.; Xi, Z. Chem. Commun. 2002, 2, 142.
(b) Zhao, C.; Yan, J.; Xi, Z. J. Org. Chem. 2003, 68, 4355.
(c) Zhao, C.; Lu, J.; Yan, J.; Xi, Z. Tetrahedron Lett. 2003, 44, 6895.
(d) Zhao, C.; Lu, J.; Li, Z.; Xi, Z. Tetrahedron 2004, 60, 1417.
[57] (a) Coperet, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695.
(b) Li, P.; Xi, Z.; Takahashi, T. Chin. J. Chem. 2001, 19, 45.
[58] Xi, Z. F.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444.
[59] Song, Z. Y.; Hsieh, Y. F.; Kanno, K.; Nakajima, K.; Takahashi, T. Organometallics 2011, 30, 844.
[60] Liao, Q.; Zhang, L.; Wang, F.; Li, S.; Xi, C. J. Eur. J. Org. Chem. 2010, 28, 5426.
[61] Famili, A.; Farona, M. F.; Thanedar, S. J. Chem. Soc., Chem. Commun. 1983, 3, 435.
[62] Doxsee, K. M.; Juliette, J. J. J.; Zientara, K.; Nieckarz, G. J. Am. Chem. Soc. 1994, 116, 2147.
[63] Altenburger, K.; Arndt, P.; Spannenberg, A.; Baumann, W.; Rosenthal, U. Eur. J. Inorg. Chem. 2013, 3200.
[64] (a) Takahashi, T.; Song, Z. Y.; Sato, K.; Kuzuba, Y.; Nakajima, K.; Ken-ichiro, K. J. Am. Chem. Soc. 2007, 129, 11678.
(b) Takahashi, T.; Kuzuba, Y. C.; Kong, F. Z.; Nakajima, K.; Xi, Z. F. J. Am. Chem. Soc. 2005, 127, 17188.
(c) Takahashi, T.; Song, Z. Y.; Hsieh, Y. F.; Nakajima, K.; Ken-ichiro, K. J. Am. Chem. Soc. 2008, 130, 15236.
[65] (a) Xi, Z. F.; Kimihiko, S.; Gao, Y.; Lu, J. M.; Tamotsu, T. J. Am. Chem. Soc. 2003, 125, 9568.
(b) Kempe, R. Angew. Chem., Int. Ed. 2004, 43, 1463.
(c) Takahashi, T.; Kanno, K. Organomet. Chem. 2004, 8, 217.
(d) Xi, Z. F.; Kong, F. Z.; Zheng, W. X.; Zhang, W. X. Chin. J. Org. Chem. 2005, 25, 229 (in Chinese).
(席振峰, 孔凡志, 郑卫新, 张文雄, 有机化学, 2005, 25, 229.)
[66] (a) Gleiter, R.; Merger, In Mordern Acetylene Chemistry, Eds.: Stang, P. J.; Diederich, F., Wiley-VCH, 1995, Chapter 8.
(b) Meier, H. Adv. Strain Org. Chem. 1991, 1, 215.
[67] (a) Suzuki, N.; Watanabe, T.; Yoshida, H.; Iwasaki, M.; Saburi, M.; Tezuka, M.; Hirose, T.; Hashizume, D.; Chihara, T. J. Organomet. Chem. 2006, 691, 1175.
(b) Bolster, J. M.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 2868.
[68] (a) Carl, A. M.; Todd, N.; Graham, J.; Cordes, A. W.; Allison, N. T. Organometallics 1988, 7, 2573.
(b) Robert, H. G.; Akira, M. J. Am. Chem. Soc. 1978, 100, 7418.
[69] Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557.
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