Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 865-875.DOI: 10.6023/cjoc201310007 Previous Articles Next Articles
Reviews
王萍, 章彦婧, 王伟, 郑卫新
收稿日期:
2013-10-10
修回日期:
2013-12-30
发布日期:
2014-01-10
通讯作者:
郑卫新
E-mail:wxzheng@hznu.edu.cn
基金资助:
国家自然科学基金(No. 20972037)、浙江省重点科技创新团队建设项目(No. 2010R50017)、杭州师范大学优秀中青年教师支持计划(No. HNUEYT 2011-01-013)、教育部创新团队“长江学者和创新团队发展计划资助(No. IRT 1231)资助项目.
Wang Ping, Zhang Yanjing, Wang Wei, Zheng Weixin
Received:
2013-10-10
Revised:
2013-12-30
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).
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Wang Ping, Zhang Yanjing, Wang Wei, Zheng Weixin. Progresses on Synthesis and Applications of Bis(cyclopentadieny)titanacycles[J]. Chin. J. Org. Chem., 2014, 34(5): 865-875.
[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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