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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 陳竹亭(Jwu-Ting Chen) | |
dc.contributor.author | I-Hsin Chang | en |
dc.contributor.author | 張益信 | zh_TW |
dc.date.accessioned | 2021-06-15T03:59:15Z | - |
dc.date.available | 2012-05-12 | |
dc.date.copyright | 2010-05-12 | |
dc.date.issued | 2010 | |
dc.date.submitted | 2010-04-21 | |
dc.identifier.citation | 1. (a) Anderson, M. P.; Casalnuovo, A. L.; Johson, B. J.; Mattson, B. M.; Mueting, A. M.; Pignolet, L. H. Inorg. Chem. 1988, 27, 1649. (b) Abu-Gnim, C.; Amer, I. J. Mol. Catal. 1993, 85, L275. (c) Zhang, Z. -Z.; Cheng, H. Coord. Chem. Rev. 1996, 147, 1. (d) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2, 200. (e) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. M.; Kru¨ ger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 889. (f) Mudalige, D. C.; Ma, E. S.; Rettig, S. J.; James, B. R.; Cullen, W. R. Inorg. Chem. 1997, 36, 5426. (g) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighhi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369. (h) Reddy, K. R.; Chen, C. L.; Liu, Y. H.; Peng, S. M.; Chen, J. T.; Liu, S. T. Organometallics 1999, 18, 2574. (i) Amatore, C.; Fuxa, A.; Jutand, A.Chem. Eur. J. 2000, 8, 1474.
2. Lappert, M. F. J. Organomet. Chem. 1988, 358, 185. 3. (a) Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361. (b) Regitz, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 725. (c) Herrmann, W. A. Angew. Chem. Int. Ed. Engl. 2002, 41, 1290. (d) Arduengo, A. J., III Acc. Chem. Res. 1999, 32, 913. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. 4. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science: Mill Valley, CA. 1987. 5. Gade, L. H.; Bellemin-Laponnaz, S. Coord. Chem. Rev. 2007, 251, 718. 6. (a) Naud, F.; Braunstein, P. Angew. Chem. Int. Ed. 2001, 40, 680. (b) Slone, C. S.; Weinberger, D. A.; Mirkin, C. A. Prog. Inorg. Chem. 1999, 48, 233. 7. (a) Danopoulos, A. A.; Tsoureas, N.; Macgregor, S. A.; Smith, C. Organometallics 2007, 26, 253. (b) Mas-Marzá, E; Sanaú, M; Peris, E. J. Organomet. Chem. 2005, 690, 5576. (c) Mas-Marzá, E.; Sanaú, M.; Peris, E. Inorg. Chem. 2005, 44, 9961. (d) Winston, S.; Stylianides, N.; Tulloch, A. A. D.; Wright, J. A.; Danopoulos, A. A. Polyhedron 2004, 23, 2813. (e) Danopoulos, A. A.; Winston, S.; Gelbricht, T.; Hursthouse, M. B.; Tooze, R. P. Chem. Commun. 2002, 482. (f) Wang, C.-Y.; Liu, Y.-H.; Peng, S.-M.; Chen, J.-T.; Liu, S.-T. J. Organomet. Chem. 2007, 692, 3976. (g) McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741. (h) Loch, J. A.; Albrecht, M.; Peris, E.; Mata, J.; Faller, J. W.; Crabtree, R. H. Organometallics 2002, 21, 700. (i) Gruendemann, S.; Albrecht, M.; Kovacevic, A.; Faller, J. W.; Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2002, 2163. (j) Tulloch, A. A. D.; Winston, S.; Danopoulos, A. A.; Eastham, G.; Hursthouse, M. B. Dalton Trans. 2003, 699. (k) Frey, G. D.; Schuetz, J.; Herdtweck, E.; Herrmann, W. A. Organometallics 2005, 24, 4416. 8. (a) Spencer, L. P.; Winston, S.; Fryzuk, M. D. Organometallics 2004, 23, 3372. (b) Arnold, P. L.; Mungur, S. A.; Blake, A. J.; Wilson, C. Angew. Chem., Int. Ed. 2003, 42, 5981. (c) Douthwaite, R. E.; Houghton, J.; Kariuki, B. M. Chem. Commun. 2004, 698. (d) Hu, X.; Meyer, K. J. Am. Chem. Soc. 2004, 126, 16322. (e) Liao, C. Y.; Chan, K. T.; Zeng, J. Y.; Hu, C. H.; Tu, C. Y.; Lee, H. M. Organometallics 2007, 26, 1692. (f) Jiménez, M. V.; Pérez-Torrente, J. J.; Bartolomé, M. I.; Gierz, V.; Lahoz, F. J.; Oro, L. A. Organometallics 2008, 27, 224. (g) Arnold, P. L.; Liddle, S. T. Chem. Commun. 2006, 3959, 3971. 9. Albert, K.; Gisdakis, P.; Rösch, N. Organometallics, 1998, 17, 1608. 10. (a) Herrmann, W. A.; Gooßen, L. J.; Spiegler, M. J. Organomet. Chem. 1997, 547, 357. (b) Arnold, P. L.; Blake, A. L.; Wilson, C. Chem. Eur. J. 2005, 11, 6095. (c) Arnold, P. L.; Scarisbrick, A. C.; Blake, A. J.; Wilson, C. Chem. Commun. 2001, 2340. (d) Mas-Marza, E.; Poyatos, M.; Sanau, M.; Peris, E. Organometallics 2004, 23, 323. (e) Waltman, A. W.; Grubbs, R. H. Organometallics 2004, 23, 3105. (f) Pruehs, S.; Lehmann, C. W.; Fuerstner, A. Organometallics 2004, 23, 280. (g) Aihara, H.; Matsuo, T.; Kawaguchi, H. Chem. Commun. 2003, 2204. (h) Chianese, A. R.; Crabtree, R. H. Organometallics 2005, 24, 4432. 11. (a) Seo, H.; Park, H. -J.; Kim, B. Y.; Lee, J. H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 618. (b) Huynh, H. V.; Yeo, C. H.; Tan, G. K. Chem. Commun. 2006, 3833. (c) Wolf, J.; Labande, A.; Daran, J. –C.; Poli, R. Eur. J. Inorg. Chem. 2007, 5069. (d) Ros, A.; Monge, D.; Alcarazo, M.; Álvarez, E.; Lassaletta, J. M.; Fernández, R. Organometallics 2006, 25, 6039. (e) Roseblade, S. J. ; Ros, A.; Monge, D.; Alcarazo, M.; Alvarez, E. ; Lassaletta, J. M.; Fernandez, R. Organometallics 2007, 26, 2570. (f) Fliedel, C.; Schnee, G.; Braustein, P. Dalton Trans. 2009, 2474. 12. Ce’sar, V.; Bellemin-Laponnaz, S.; Wadepohl, H.; Gade, L. H. Chem. Eur. J. 2005, 11, 2862. 13. Ce’sar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Eur. J. Inorg. Chem. 2004, 3436. 14. Yuan, Y.; Raabe, G.; Bolm, C. J. Organomet. Chem. 2005, 690, 5747. 15. Poyatos, M.; Maisse-Francüois, A.; Bellemin-Laponnaz, S.; Gade, L. H. Organometallics 2006, 25, 2634. 16. (a) Ye , J. S.; Chen, W. Z.; Wang, D. Q. Dalton. Trans. 2008, 30, 4015. (b) Bella, A. F.; Ruiz, A.; Claver, C.; Sepu’lveda, F.; Jalo’n, F. A.; Manzano, B. R. J. Organomet. Chem. 2008, 693, 1269. (c) Chen, C.; Qiu, H.; Chen, W.; Wang, D. J. Organomet. Chem. 2008, 693, 3273. (d) Lee, K. M.; Chen, J. C. C.; Lin, I. J. B. J. Organomet. Chem. 2001, 617-618, 364 (e) Meyer, D.; Taige, M. A.; Zeller, A.; Hohlfeld, K.; Ahrens, S.; Strassner, T. Organometallics 2009, 28, 2142. 17. (a) Tsoureas, N.; Danopoulos, A. A.; Tulloch, A. A. D.; Light, M. E. Organometallics 2003, 22, 4750. (b) Lee, H. M.; Zeng, J. Y.; Hu, C.-H.; Lee, M.-T. Inorg. Chem. 2004, 43, 6822. (c) Wang, A.-E.; Zhong, J.; Xie, J.-H.; Li, K.; Zhou, Q.-L. Adv. Synth. Catal. 2004, 346, 595. (d) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511. (e) Herrmann, W. A.; Koecher, C.; Goossen, L. J.; Artus, G. R. J. Chem. Eur. J. 1996, 2, 1627. (f) Lee, C. C.; Ke, W. C.; Chan, K. T.; Lai, C. L.; Hu, C. H.; Lee, H. M. Chem. Eur. J. 2007, 13, 582 (g) Hahn, F. E.; Jahnke, M. C.; Pape, T. Organometallics 2006, 25, 5927. (h) Labande, A.; Daran, J. –C.; Manoury, E.; Poli, R. Eur. J. Inorg. Chem. 2007, 1205. (i) Tsoureas, N.; Danopoulos, A. A.; Tulloch, A. A. D.; Light, M. E. Organometallics 2003, 22, 4750. (j) Wang, A.-E.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. Tetrahedron 2005, 61, 259. 18. (a) Tulloch, A. A. D.; Danopoulos, A. A.; Tizzard, G. J.; Coles, S. J.;Hursthouse, M. B.; Hay-Motherwell, R. S.; Motherwell, W. B. Chem. Commun. 2001, 1270. (b) Gru¨ndemann, S.; Albrecht, M.; Loch, J. A.; Faller, J. W.; Crabtree, R. H. Organometallics 2001, 20, 5485. 19. (a) McGuiness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029. (b) Nielsen, D. J.; Magill, A. M.; Yates, B. F.; Cavell, K. J.; Skelton, B. W.; White, A. H. Chem. Commun. 2002, 2500. 20. Liu, J. P.; Chen, J. B.; Zhao, Y. H.; Li, L.; Zhang, H. B. Synthesis 2003, 17, 2661. 21. Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972. 22. Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978. 23. Appelhans, L. N.; Zuccaccia, D. Kovacevic, A.; Chianese, A. R.; Miecznikowski, J. R.; Macchioni, A.; Clot, E.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2005, 127, 16299. 24. (a) Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228. (b) Sandstro, J. Dynamic NMR Spectroscopy, p. 1. Academic Press, New York, 1982. (c) Sandstro, J. Dynamic NMR Spectroscopy, p. 93. Academic Press, New York, 1982. 25. Modarresi-Alam, A. R.; Keykha, H.; Khamooshi, F.; Dabbagh, H. A. Tetrahedron 2004, 60, 1525. 26. (a) Abel, E. W.; Evans, D, G; Koe, J. R.; Sik, V.; Hursthome, M. B.; Bates, P. A. Dalton Trans. 1989, 11, 2315. (b) Abel, E. W.; Dormer, J. C.; Ellis, K. J.; Hursthome, M. B.; Mazid, M. A. Dalton Trans. 1992, 1073. 27. (a) Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Bandoli, G. Organometallics 2000, 19, 1461. (b) Canovese, L.; Visentin, F.; Chessa, G.; Santo, C.; Ugagliati, P.; Bandoli, G. J. Organomet. Chem. 2002, 650, 43. (c) Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Santo, C.; Bandoli, G.; Maini, L. Organometallics 2003, 22, 3230. 28. (a) Danopoulos, A. A.; Winston, S.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans., 2002, 3090. (b) Stylianides, N.; Danopoulos, A. A.; Tsoureas, N. J. Organomet. Chem. 2005, 690, 5948. 29. Wang, X.; Liu, S.; Weng, L.-H.; Jin, G.-X. Organometallics 2006, 25, 3565. 30. Ojima, I.; Li, Z.; Zhu J. in The Chemistry of Organic silicon Compounds (Eds.: Rappoport Z., Apeloig Y.), Wiley, New York, 1998, vol. 2, p. 1687. 31. (a) Ojima, I.; Nihonyanagi, M.; Nagai, Y. J. Chem. Soc. Chem.Commun. 1972, 938. (b) Corriu, R. J. P.; Moreau, J. J. E. J. Organomet. Chem. 1975, 91, C27. (c) Ojima, I.; Nihonyanagi, M.; Kogure, T.; Kumagai, M.; Horiuchi S.; Nakatsugawa, K. J. Organomet. Chem. 1975, 94, 449. (d) Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390–1399. 32. (a) Dumont, W.; Poulin, J. C.; Tuan P., Dang; Kagan, H. B. J. Am.Chem. Soc. 1973, 95, 8295. (b) Wright, M. E.; Svejda, S. A. Polyhedron 1991, 10, 1061. (c) Brunner, H.; Riepl, G.; Weitzer, H. Angew. Chem. 1983, 95, 326. (d) Brunner, H.; Becker, R.; Riepl, G. Organometallics 1984, 3, 1354. (e) Brunner, H.; Reiter, B.; Riepl, G. Chem. Ber. 1984, 117, 1330. (f) Brunner, H.; Kürzinger, A. J. Organomet. Chem. 1988, 346, 413. (g) Kogure, T.; Ojima, I. J. Organomet. Chem. 1982, 234, 249. (h) Tao, B.; Fu, G. C. Angew. Chem. Int. Ed. Engl. 2002, 41, 3892. (i) Corriu, R.; Moreau, J. J. E. J. Organomet. Chem. 1975, 85, 19. (j) Ojima, I.; Kogure, T.; Kumagai, M.; Horiuchi, S.; Sato, T. J. Organomet. Chem. 1976, 122, 83. (k) Reyes, C.; Prock, A.; Giering, W. P. Organometallics 2002, 21, 546. (l) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. 33. (a) Chan, T. H.; Zheng, G. Z. Tetrahedron Lett. 1993, 34, 3095. (b) Zheng, G. Z.; Chan, T. H. Organometallics 1995, 14, 70. 34. (a) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. (b) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (c) Nishiyama, H.; Park, S. B.; Itoh, K. Tetrahedron: Asymmetry 1992, 3, 1029. (d) Cuervo, D.; Gamasa, M. P.; Gimeno, J. J. Mol. Catal. A 2006, 249, 60. 35. (a) Hayashi, T.; Yamamoto, K.; Kasuga, K.; Omizu, H.; Kumada, M. J. Organomet. Chem. 1976, 113, 127. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem. Int. Ed. 1994, 33, 111. (c) Imamoto, T.; Itoh, T.; Yamanoi, Y.; Narui, R.; Yoshida, K. Tetrahedron: Asymmetry 2006, 17, 560. (d) Kolb, I.; Hetflejs, J. Collect. Czech. Chem. Commun. 1980, 45, 2808. (e) Waldman, T. E.; Schaefer, G.; Riley, D. P. ACS Symp. Ser. 1993, 517, 58. 36. Faller, J. W.; Fontaine, P. P. Organometallics 2006, 25, 5887. 37. Nonnenmacher, M.; Kunz, D.; Rominger, F. Organometallics 2008, 27, 1561. 38. (a) Reyes, C.; Prock, A.; Giering, W. P. Organometallics 2002, 21,546. (b) Kolb, I.; Hetflejs, J. Collect. Czech. Chem. Commun. 1980, 45, 2808. (c) Waldman, T. E.; Schaefer, G.; Riley, D. P. ACS Symp. Ser. 1993, 517, 58 39. Rhodium Catalyzed Hydroformylation; Claver, C., van Leeuwen, P. W. N. M., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 2000. 40. Roelen, O. Ger. Offen. 1938, 849,548. 41. Coloquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, London, 1991. 42. Pruett, R. L. Adv. Organomet. Chem. 1979, 17, 1. 43. Chen, A. C.; Ren, L.; Decken, A.; Crudden, C. M. Organometallics 2000, 19, 3459. 44. Poyatos, M.; Uriz, P.; Mata, J. A.; Claver, C.; Fernandez, E.; Peris, E. Organometallics 2003, 22, 440. 45. Gil, W.; Trzeciak, A. M.; Zio´łkowski, J. J. Organometallics 2008, 27, 4131. 46. Praetoriu, J. M.; Kotyk, M. W.; Webb, J. D.; Wang, R. Y.; Crudden C. M. Organometallics 2007, 26, 1051. 47. (a) Bayon, J. C.; Claver, C.; Masdeu-Bulto, A. M. Coord. Chem. Rev. 1999, 193–195, 73. (b) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (c) Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133. 48. Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. 49. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. 50. Herrmann, W. A.; Kocher, C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2162. 51. Ma, Y. D.; Song, C.; Ma, C. Q.; Sun, Z. J.; Chai, Q.; Andrus, M. B. Angew. Chem. Int. Ed. 2003, 42, 5871. 52. Becht, J. –M.; Bappert, E.; Helmchen, G. Adv. Synth. Catal. 2005, 347, 1495. 53. Zigterman, J. L.; Woo, J. C. S.; Walker, S. D.; Tedrow, J. S.; Borths, C. J.; Bunel, E. E.; Faul, M. M. J. Org. Chem. 2007, 72, 8870. 54. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. 55. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992. 56. (a) Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533. (b) Ho, T.-L. Chem. Rev. 1975, 75, 1. (c) Hegedus, L. L.; McCabe, R. W. Catalyst Poisoning; Marcel Dekker: New York, NY, 1984; (d) Dubois, M. R. Chem. Rev. 1989, 89, 1. (e) Mare’ cot, P.; Paraiso, E.; Dumas, J. M.; Barbier, J. Appl. Catal. A: Gen. 1992, 80, 79. 57. For reviews on the synthesis of ring systems using [2+2+2] cycloadditions see: (a) Kotha, S.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (c) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307. (d) Tanaka, K. Synlett 2007, 10, 1977. (e) Shibata, T.; Tsuchikama, K. Org. Biomol. Chem. 2008, 6, 1317. (f) Yamamoto, Y. Curr. Org. Chem. 2005, 9, 503. (g) Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085. (h) Varela, J. A.; Sa_, C. Chem. Rev. 2003, 103, 3787. (i) Henry, G. D. Tetrahedron 2004, 60, 6043. (j) Agenet, N.; Busine, O.; Slowinski, F.; Gandon, V.; Aubert, C.; Malacria, M. Org. React. 2007, 68, 1. 58. Cadierno, V.; Garcı´a-Garrido, S. E.; Gimeno, H. J. Am. Chem. Soc. 2006, 128, 15094. 59. Chen, L.; Li, C.-J. Adv. Synth. Catal. 2006, 348, 1459. 60. For a review on transition-metal catalyzed alkyne hydration see: Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079. 61. (a) Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (c) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69. (d) Herrmann, W. A.; Öfele, K.; von Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229. (e) Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366. (f) Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239. 62. (a) Chiu, P. L.; Lai, C.-L.; Chang, C.-F.; Hu, C.-H.; Lee, H. M. Organometallics 2005, 24, 6169. (c) Lee. H. M.; Chiu, P. L.; Zeng, J. Y. Inorg. Chim. Acta 2004, 357, 4313. 63. Ke´gl, T.; Kolla´r, L. J. Mol. Catal. A: Chem. 1997, 122, 95. 64. (a) Wang, X.; Liu, S.; Jin, G.-X. Organometallics 2004, 23, 6002. (c) Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Organometallics 2005, 24, 4241. 65. Guzel, B.; Omary, M. A.; Fackler Jr., J. P.; Akgerman, A. Inorg. Chim. Acta 2001, 325, 45. 66. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997. 67. Bayersdo¨rfer, R.; Ganter, B.; Englert, B.; Keim, W.; Vogt, D. J. Organomet. Chem. 1998, 552, 187. 68. Wilke, G.; Angermund, K.; Fink, G.; Kru¨ ger, C.; Leven, T.; Mollbach, A.; Monkiewicz, J.; Rink, S.; Schwager, H.; Walter, K. H. In New aspects of organic chemistry II; Yoshida, Z., Oshiro,Y., Eds.; Kodansha: Tokyo, 1992. 69. Angermund, K.; Eckerle, A.; Lutz, F. Z. Naturforsch. 1995, 50b, 488. 70. Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089. 71. Yoshida, T.; Tani, K.; Yamagata, T.; Tatsuno, Y.; Saito, T. J. Chem. Soc., Chem. Commun. 1990, 292. 72. Datt, M. S.; Nair, J. J.; Otto, S. J. Organomet. Chem. 2005, 690, 3422. 73. Dyson, G.; Frison, J. G.; Simonovic, S.; Whitwood, A. C.; Douthwaite, R. E. Organometallics 2008, 27, 281. 74. Lee, W. –Z.; Wang, T. –L.; Tsang, H. –S.; Liu, C. –Y.; Chen, C. –T. Organometallics 2009, 28, 652. 75. Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697. | |
dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/44951 | - |
dc.description.abstract | 在本論文中,含半易變異原子碳烯雙芽配基釕金屬錯合物可以當作勻相催化劑應用於矽氫加成反應、氫甲醛化反應、共軛加成反應和環化加成反應。
含異原子碳烯雙芽配位基釕金屬錯合物是以化學式[Rh(COD)LN-C]+X-或是以化學式[Rh(COD)LS-C]+X-所組成,而這些錯合物合成採用將銀碳烯錯合物做金屬轉值反應到釕金屬前驅物上。且釕金屬錯合物(4a-4i)在碳譜上碳烯碳的化學位移在176-177 ppm,而釕碳的耦合常數為53-54 Hz,嘧啶碳烯雙芽配位基釕金屬錯合物對於矽氫加成到苯乙酮反應有很好的反應活性(產率為98%)。 在室溫的氫譜中,錯合物4a的1,5-環辛二烯上的烯的氫譜是寬的且硫醚側臂的亞甲基的氫譜呈現單一鋒,變溫核磁共振光譜技術可以被採用來研究這些現象,並根據Gutowsky-Holm和Eyring公式可計算出硫原子反轉的自由能為48.61KJmol-1。 含有硫醚碳烯雙芽配位基的釕金屬錯合物對氫甲醛化芳香烯烴或脂肪烯烴反應是很有效率的催化劑,但是它的產物醛的直鏈/支鏈比是差不多的,比值差不多是1,可以藉由加入磷配位基來調控產物醛的直鏈/支鏈比,並可將產物得到全部都是支鏈醛的產物但是只有25%的轉換率,合成氣體的壓力可以被調降到300 psi,而氫甲醛化反應的轉換率是定量生成的和產物醛的直鏈/支鏈比值在0.93-1.23。 含有硫醚碳烯雙芽配位基的釕金屬錯合物對硼酸共軛加成到 | zh_TW |
dc.description.abstract | In this thesis, the cationic rhodium (I) complexes bearing with hemilabile NHC bidentate ligands have been developed for the service as homogeneous catalysts using in the reactions such as hydrosilylation, hydroformylation, conjugate addition, and cycloaddition is studied.
The cationic rhodium (I) complexes bearing NHC bidentate ligands in the form of [Rh(COD)LN-C]+X- or in the form of [Rh(COD)LS-C]+X- are successfully synthesized via transmetalation of silver NHC complex to cationic rhodium (I) metal source. The rhodium carbene carbon of the cationic rhodium (I) complexes (4a-4i) show 13C NMR resonance in 176.0-177.0 ppm and JRh-C = 53.0-54.0 Hz. The cationic rhodium (I) pyrimidyl NHC complexes display excellent catalytic activity for the hydrosilytion of acetophenones.(98% yield) The proton NMR of 4a shows the broad peaks in the COD and the singlet peak of the methylene protons of the thioether side arm at room temperature. To study the phenomenon in the solution containing 4a, the variable temperature NMR spectra are measured. According to the Gutowsky-Holm relationship24 and Eyring equation, the free energy of the sulfur inversion can be calculated in 48.61 KJmol-1. The rhodium (I) thioether NHC complexes can be effective catalysts for hydroformylation of aromatic or aliphatic olefins, but the selectivity of linear/branch aldehydes is fair (the ratio of linear/branch is almost 1). By adding phosphines, we can tune the ratio of linear/branch to be all branched aldehyde but the conversion is low (25% conversion). We can reduce the pressure of syn gas (H2/CO=1/1) to 300 psi instead of high pressure (1000 psi). The conversion of the hydroformylation can be quantitative and the ratio of the linear/branched aldehyde can be 0.93-1.23. The rhodium (I) thioether NHC complexes are efficient catalysts for the conjugate addition of boronic acids to enones. The catalyst loading was reduced to 0.5 mol% instead of the 3 mol% catalyst loading. The electron deficient or electron rich aryl boronic acids cannot retard the reaction. In spite of the bulky substituent such as o-methoxyphenyl boronic acid, the yield of Michael addition product was obtained in quantitative yield (98%). If thiol replaced the boronic acid, the thia- Michael addition can also be excellent yied (95%) by using rhodium thioether carbene catalyst. [2+2+2] Cycloaddition of DEAD or DMAD can be achieved in aqueous solution by using rhodium (I) thioether carbene catalyst. The DEAD and diyne can be different alkyne moiety and cyclotrimerize to form the cyclic benezene derivative. Pd (II) complexes bearing bidentate pyrimidyl-N-heterocyclic carbene ligands in the form of [LN-C]PdCl2 (LN-C = 2-pyrimidyl-imidazolylidene-NR, R = Me (5a), PhCH2 (5b), 2,6-Me2C6H3 (5d), 2,4,6-Me3C6H2 (5c)) have been synthesized and structurally characterized. The pyrimidyl-NHC ligand can facilitate these complexes for Suzuki-Miyaura cross coupling of aryl bromides and boronic acids. | en |
dc.description.provenance | Made available in DSpace on 2021-06-15T03:59:15Z (GMT). No. of bitstreams: 1 ntu-99-D93223009-1.pdf: 7264446 bytes, checksum: bd2d2443cf553b6ea714b523663de3d9 (MD5) Previous issue date: 2010 | en |
dc.description.tableofcontents | 謝誌 i
Abstract ii 摘要 v Content vii List of Tables x List of Schemes xiv List of Figures xviii Chapter 1 Introduction 1 1-1 Hemilabile Bidentate Ligand 1 1-2 Rhodium (I) Metal Complexes Bearing with Hemilabile Bidentate NHC Ligands 5 1-3 Palladium (II) Metal Complexes Bearing with Hemilabile Bidentate NHC Ligands 12 1-4 Strategy and Goal of This Research 20 Chapter 2 Synthesis of the Hemilabile Bidentate Heterotopic Ligand 23 2-1 Synthesis of N-Aryl Substituted Imidazoles 23 2-2 Synthesis of Thioether Imidazolium Salts 25 2-3 Synthesis of Pyrimidine Imidazolium Salts 28 2-4 Summary 31 Chapter 3 Synthesis of the Late Transition Metal Complexes Bearing Hemilabile Heterotopic Bidentate NHC Ligands 32 3-1 Synthesis of Silver NHC Complexes 32 3-1-1 Synthesis of Silver Thioether NHC Complexes 32 3-1-2 Synthesis of Silver Pyrimidyl NHC Complexes 36 3-2 Synthesis of Cationic Rhodium (I) NHC Complexes 38 3-2-1 Synthesis of Cationic Rhodium (I) Thioether NHC Complexes 38 3-2-2 Synthesis of Cationic Rhodium (I) Pyrimidyl NHC Complexes 52 3-3 Synthesis of Palladium Pyrimidyl NHC Complexes 58 3-4 Summary 66 Chapter 4 Catalysis by Using Hemilabile Heterotopic Bidentate NHC Ligands of Their Late Transition Metal Complexes 68 4-1 Application of Cationic Rhodium (I) NHC Complexes to Catalysis 68 4-1-1 Hydrosilylation 68 4-1-2 Hydroformylation 73 4-1-3 Conjugate Addition of Aryl Boronic Acids to Enones 89 4-1-4 Thia-Michael Addition to Enones 106 4-1-5 [2+2+2] Cycloaddition of Alkyne Derivatives 109 4-2 Application to Suzuki Miyaura Coupling Reaction by Using Palladium Pyrimidyl NHC Complexes 116 4-3 Summary 119 Chapter 5 Conclusions 122 Chapter 6 Experimental Section 127 References 165 Appendix 178 | |
dc.language.iso | en | |
dc.title | 含異原子雙芽碳烯配位基及其後過渡金屬錯合物合成與催化反應研究 | zh_TW |
dc.title | Heterotopic Bidentate NHC Ligands and Their Late Transition Metal Complexes-Synthesis and Catalysis | en |
dc.type | Thesis | |
dc.date.schoolyear | 98-2 | |
dc.description.degree | 博士 | |
dc.contributor.oralexamcommittee | 林英智,蔡蘊明,劉陵崗,李漢文 | |
dc.subject.keyword | 碳烯,銠,鈀,共軛加成,耦合,環化加成, | zh_TW |
dc.subject.keyword | NHC,rhodium,palladium,congugate addition,hydroformylation,coupling, | en |
dc.relation.page | 219 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2010-04-21 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
顯示於系所單位: | 化學系 |
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