Polycondensation reaction using the Tsuji-Trost reaction, and a new aspect of the polycondensation via controlled reaction pathways

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 65, Issue 4, 2007, Pages 334-346

  Nomura, Nobuyoshi ^a   Tsurugi, Ko ^a   Yoshida, Nao ^a   Komiyama, Susumu ^a   Okada, Masahiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Allylic ester; Carothers Flory equation; Catalysis; Condensation reaction; Degree of polymerization; Palladium; Polycondensation; Reaction pathway; Stoichiometric balance; Tsuji Trost reaction

Indexed keywords

AMIDES; CATALYSIS; CONDENSATION REACTIONS; ESTERS; PALLADIUM; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

ALLYLIC ESTERS; CAROTHERS-FLORY EQUATION; DEGREE OF POLYMERIZATION; REACTION PATHWAY; TSUJI-TROST REACTION;

POLYCONDENSATION;

EID: 34547311908     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.65.334     Document Type: Article

References (92)

1. Japanese source
2. (b) J. Tsuji, J. Synth. Org. Chem., Jpn., 63, 539 (2005);
3. (c) idem, ibid., 60, 989 (2002);
4. (d) idem, i&id, 59, 607(2001)
5. (a) J. Tsuji, Transition Metal Reagents and Catalysts, John Wiley & Sons, Chichester, (2000);
6. (b) J. Tsuji, ed. Perspectives in Organopalladium Chemistry for the XXI Century, Elsevier, Lausanne (1999)
7. Japanese source
8. B. M. Trost, T. R. Verhoeven, J. M. Fortunak, Tetrahedron Lett, 20, 2301 (1979);
9. (b) Y. I. M. Nilsson, P. G. Andersson, J.-E. Bäckvall, J. Am. Chem. Soc., 115, 6609 (1993)
10. (a) J. Zhou, G. C. Fu, J. Am. Chem. Soc., 125, 12527 (2003).
11. (b) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, ibid., 125, 5646 (2003).
12. J. Smid, W. Hafner, Angew Chem., 71, 284 (1959)
13. J. Tsuji, H. Takahashi, M. Morikawa, Tetrahedron Lett., 6, 4387 (1965)
14. (a) G. Hata, K. Takahashi, A. Miyake, J. Chem. Soc., Chem. Commun., 1970, 1392;
15. K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn., 45, 230 (1972);
16. (b) K. E. Atkins, W. E. Walker, R. M. Manyik, Tetrahedron Lett., 11, 3821 (1970)
17. B. M. Trost, P. E. Strege, J. Am. Chem. Soc., 99, 1649 (1977)
18. (a) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron, 56, 5959 (2000);
19. (b) B. M. Trost, D. L. Van Vranken, Chem. Rev., 96, 395 (1996);
20. (c) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry, 3, 1089 (1992)
21. B. M. Trost, M. L. Crawley, Chem. Rev., 103, 2921 (2003)
22. (a) W. H. Carothers, Trans. Faraday Soc., 32, 39 (1936);
23. (b) P. J. Flory, J. Am. Chem. Soc., 58, 1877 (1936);
24. (c) idem, Chem. Rev., 39, 137 (1946)
25. (a) M. Suzuki, S. Sawada, T. Saegusa, Macromolecules, 22, 1505 (1989);
26. (b) M. Suzuki, A. Ii, T. Saegusa, ibid., 25, 7071 (1992);
27. (c) M. Suzuki, S. Sawada, S. Yoshida, A. Eberhardt, T. Saegusa, ibid., 26, 4748 (1993);
28. (d) M. Suzuki, J. Synth. Org. Chem., Jpn., 51, 141, (1993)
29. (a) M. Bochmann, K. Kelly, J. Chem. Soc., Chem. Commun. 1989, 532;
30. (b) M. Bochmann, K. Kelly, J. Lu, J. Polym. Sci., Part A: Polym. Chem., 30, 2511 (1992)
31. (a) N. Miyaki, I. Tomita, T. Endo, Macromolecules, 29, 6685 (1996);
32. (b) idem, J. Polym. Sci., Part A: Polym. Chem., 35, 2097 (1997)
33. S. Kacker, A. Sen, J. Am. Chem. Soc., 119, 10028 (1997)
34. (a) D. Takeuchi, S. Kim, K. Osakada, Angew. Chem. Int. Ed., 40, 2685 (2001);
35. (b) S. Kim, D. Takeuchi, K. Osakada, Macromol Chem. Phys., 204, 666 (2003);
36. (c) D. Takeuchi, A. Inoue, K. Osakada, M. Kobayashi, K. Yamaguchi, Organometallics, 25, 4062 (2006)
37. (a) T. Koizumi, J. Sakamoto, Y. Gondo, T. Endo, Macromolecules, 33, 7235 (2000);
38. (b) idem, J. Polym. Sei, Part A: Polym. Chem., 40, 2487 (2002);
39. (c) idem, Macromolecules, 35, 2898 (2002);
40. (d) T. Koizumi, T. Imai, T. Endo, J. Polym. Sci., Part A: Polym. Chem., 41, 476 (2003);
41. (e) T. Koizumi, Y. Koma, T. Endo, Macromolecules, 36, 5882 (2003);
42. (f) T. Koizumi, T. Akita, H. Nishino, T. Endo, Polym. J., 36, 647 (2004)
43. (a) N. Nomura, Y. C. Mermet-Bouvier, T. V. RajanBabu, Synlett, 1996, 754;
44. (b) D. S. Clyne, Y. C. Mermet-Bouvier, N. Nomura, T. V. RajanBabu, J. Org. Chem., 64, 7601 (1999)
45. Japanese source
46. Japanese source
47. N. Nomura, K. Tsurugi, M. Okada, J. Am. Chem. Soc., 121, 7268 (1999)
48. (a) E. Negishi, H. Matsushita, S. Chatterjee, R. A. John, J. Org. Chem., 47, 3188 (1982);
49. (b) E. T. Luo, E. Negsihi, Tetrahedron Lett., 26, 2177 (1985)
50. N. Nomura, K. Tsurugi, N. Yoshida, M. Okada, Curr. Org. Syn., 2, 21 (2005)
51. Japanese source
52. N. Nomura, N. Yoshida, K. Tsurugi, K. Aoi, Macromolecules, 36, 3007 (2003)
53. K. M. Stridsberg, M. Ryner, A.-C. Albertsson, Adv. Polym. Sci., 157, 41 (2002)
54. 3N & : (a) P. G. Andersson, S. Schab, Organometallics, 14, 1 (1995);
55. (b) J. M. Takacs, E. C. Lawson, F. Clement, J. Am. Chem. Soc., 119, 5956 (1997);
56. (c) G. R. Cook, P. S. Shanker, Tetrahedron Lett., 39, 4991 (1998)
57. M. Yokoe, K. Aoi, M. Okada, J. Polym. Sei., Part A: Polym. Chem., 43, 3909 (2005).
58. Y. Furukawa, Inventing Polymer Science, Univ. of Pennsylvania, Philadelphia (1998)
59. Japanese source
60. (a) V. Percec, ACS Symposium Series 326, American Chemical Society, Washington, D.C. (1987), p 96;
61. (b) S. Boileau, New Methods for Polymer Synthesis, W. J. Mijs, ed., Plenum, New York (1992), p 179
62. K. Kimura, S. Kohama, Y. Yamashita, Macromolecules, 36, 5043 (2003)
63. N. Kihara, S.-i. Komatsu, T. Takata, T. Endo, Macromolecules, 32, 4776 (1999)
64. N. Nomura, K. Tsurugi, M. Okada, Angew. Chem. Int. Ed., 40, 1932 (2001)
65. K. Tsurugi, N. Nomura, K. Aoi, Tetrahedron Lett., 43, 469 (2002)
66. NMR (a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem., Int. Ed. Engl., 36, 2108 (1997);
67. (b) G. Helmchen, J. Organomet. Chem., 576, 203 (1999)
68. (a) A. Devasagayaraj, T. Stüdenmann, P. Knochel, Angew. Chem., Int. Ed. Engl, 34, 2723 (1996);
69. (b) K. M. Miller, T. F. Jamison, J. Am. Chem. Soc., 126, 15342 (2004)
70. N. Nomura, K. Tsurugi, T. V. RajanBabu, T. Kondo, J. Am. Chem. Soc., 126, 5354 (2004)
71. TTR: (a) Y. Tanigawa, K. Nishimura, A. Kawasaki, S.-I. Murahashi, Tetrahedron Lett., 23, 5549 (1982);
72. (b) J. P. Genêt, B. Balabane, J. E. Bäckvall, J. E. Nyström, ibid., 24, 2745 (1983)
73. (a) Z. Tan, E.-i. Negishi, Angew. Chem. Int. Ed., 45, 762 (2006);
74. (b) A. Minato, K. Suzuki, K. Tamao, J. Am. Chem. Soc., 109, 1257 (1987);
75. (c) J. Uenishi, K. Matsui, H. Ohmiya, J. Organomet. Chem., 653, 14 (2002)
76. (a) Z. Tan, E.-i. Negishi, Angew. Chem. Int. Ed., 45, 762 (2006);
77. (b) C.-G. Dong, Q.-S, Hu, J. Am. Chem. Soc., 127, 10006 (2005);
78. (c) D. Strawser, A. Karton, O. V. Zenkina, M. A. Iron, L. J. W. Shimon, J. M. Martin, M. E. van der Boom, ibid., 127, 9322 (2005);
79. (d) D. Sinclair, M. S. Sherburn, J. Org. Chem., 70, 3730 (2005);
80. (e) K. Oguma, M. Miura, T. Satoh, M. Nomura, J. Am. Chem. Soc., 122, 10464 (2000)
81. Japanese source
82. T. Koizumi, K. Sugie, O. Kiyonaga, M. Yamanaka, S. Kawabata, Macromolecules, 37, 9670 (2004)
83. T. Yokozawa, A. Yokoyama, Polym. J., 36, 65 (2004)
84. (a) K.-i. Iwashita, A. Yokoyama, T. Yokozawa, J. Polym. Sci., Part A: Polym. Chem., 43, 4109 (2005);
85. (b) R. Miyakoshi, A. Yokoyama, T. Yokozawa, J. Am. Chem. Soc., 127, 17542 (2005);
86. (c) Y. Shibasaki, T. Araki, R. Nagahata, M. Ueda, Eur. Polym. J., 41, 2428 (2005);
87. (d) R. Sugi, A. Yokoyama, T. Furuyama, M. Uchiyama, T. Yokozawa, J. Am. Chem. Soc., 127, 10172 (2005);
88. (e) A. Tanatani, A. Yokoyama, I. Azumaya, Y. Takakura, C. Mitsui, M. Shiro, M. Uchiyama, A. Muranaka, N. Kobayashi, T. Yokozawa, ibid., 127, 8553 (2005);
89. (f) T. Yokozawa, D. Muroya, R. Sugi, A. Yokoyama, Macromol. Rapid Commun., 26, 979 (2005);
90. (g) K. Yamazaki, A. Yokoyama, T. Yokozawa, Macromolecules, 39, 2432 (2006)
91. I. Mita, R. F. T. Stepto, U. W. Surer, Pure Appl. Chem., 66, 2483 (1994)
92. Japanese source