Generation of carbanions through stibine-metal and bismuthine-metal exchange reactions and its applications to precision synthesis of ω-end-functionalized polymers

Chemistry - A European Journal

Volumn 17, Issue 19, 2011, Pages 5272-5280

  Kayahara, Eiichi ^a   Yamada, Hiroto ^a   Yamago, Shigeru ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

antimony; bismuth; carbanions; metalation; polymerization

Indexed keywords

ALKYLLITHIUMS; BISMUTHINE; CARBANIONS; CHEMO-SELECTIVITY; CHEMOSELECTIVE; CONTROLLED MOLECULAR WEIGHT; ELECTROPHILES; END GROUPS; END-FUNCTIONALIZED POLYMERS; END-GROUP FUNCTIONALITY; EXCHANGE REACTION; HETEROATOMS; HIGH REACTIVITY; LIVING POLYMERS; LIVING RADICAL POLYMERIZATION; MAGNESIUM HALIDES; METAL EXCHANGE REACTIONS; METALATIONS; N-ISOPROPYLACRYLAMIDES; ORGANOMETALLIC REAGENT; POLAR FUNCTIONAL GROUPS; POLY(2-HYDROXYETHYL METHACRYLATE); POLY(BUTYL ACRYLATE);

ACRYLIC MONOMERS; ALKYLATION; AMIDES; BISMUTH; BISMUTH COMPOUNDS; ESTERS; FREE RADICAL POLYMERIZATION; FUNCTIONAL GROUPS; IONS; LIVING POLYMERIZATION; MAGNESIUM; METALS; MOLECULAR WEIGHT DISTRIBUTION; ORGANOMETALLICS; POLYMERS; SYNTHESIS (CHEMICAL);

FUNCTIONAL POLYMERS;

EID: 79955012064     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100265     Document Type: Article

References (82)

1. E. Negishi, Organometallics in Organic Synthesis, Vol. 1, Wiley, New York, 1980, pp. 91-285.
2. Main Group Metals in Organic Synthesis (Eds.:, H. Yamamoto, K. Oshima,), Wiley-VCH, Weinheim, 2005.
3. T. Kauffmann, Top. Curr. Chem. 1980, 92, 109-147.
4. T. Kauffmann, Angew. Chem. 1982, 94, 401-420
5. Angew. Chem. Int. Ed. Engl. 1982, 21, 410-429.
6. W. E. Parham, C. K. Bradsher, Acc. Chem. Res. 1982, 15, 300-305.
7. N. Sotomayor, E. Lete, Curr. Org. Chem. 2003, 7, 275-300.
8. C. Najera, M. Yus, Curr. Org. Chem. 2003, 7, 867-926.
9. P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. 2003, 115, 4438-4456
10. Angew. Chem. Int. Ed. 2003, 42, 4302-4320.
11. R. Chinchilla, C. Najera, M. Yus, Chem. Rev. 2004, 104, 2667-2722.
12. M. Schlosser, Angew. Chem. 2005, 117, 380-398
13. Angew. Chem. Int. Ed. 2005, 44, 376-393.
14. D. Seyferth, Organometallics 2006, 25, 2-24.
15. D. Seyferth, Organometallics 2009, 28, 2-33.
16. H. Gilman, H. L. Yablunky, A. C. Svigoon, J. Am. Chem. Soc. 1939, 61, 1170-1172.
17. H. Gilman, H. L. Yale, J. Am. Chem. Soc. 1950, 72, 8-10.
18. T. V. Talalaeva, K. A. Kocheshkov, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1953, 263-266.
19. G. Wittig, A. Maercker, J. Organomet. Chem. 1967, 8, 491-494.
20. F. Steinseifer, T. Kauffmann, Angew. Chem. 1980, 92, 746-747
21. Angew. Chem. Int. Ed. Engl. 1980, 19, 723-724.
22. H. Suzuki, T. Murafuji, J. Chem. Soc. Chem. Commun. 1992, 1143-1144.
23. H. J. Reich, D. P. Green, N. H. Phillips, J. Am. Chem. Soc. 1991, 113, 1414-1416.
24. H. J. Reich, D. P. Green, N. H. Phillips, J. P. Borst, I. L. Reich, Phosphorus Sulfur Silicon Relat. Elem. 1992, 67, 83-97.
25. T. Kanda, S. Kato, N. Kambe, Y. Kohara, N. Sonoda, J. Phys. Org. Chem. 1996, 9, 29-34.
26. H. J. Reich, N. H. Phillips, I. L. Reich, J. Am. Chem. Soc. 1985, 107, 4101-4103.
27. H. J. Reich, N. H. Phillips, J. Am. Chem. Soc. 1986, 108, 2102-2103.
28. H. J. Reich, D. P. Green, N. H. Phillips, J. Am. Chem. Soc. 1989, 111, 3444-3445.
29. S. Ogawa, Y. Masutomi, T. Erata, N. Furukawa, Chem. Lett. 1992, 2471-2474.
30. N. S. Zefirov, D. I. Makhon′kov, Chem. Rev. 1982, 82, 615-624.
31. S. Ogawa, S. Sato, N. Furukawa, Tetrahedron Lett. 1992, 33, 7925-7928.
32. S. Yamago, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 1-12.
33. S. Yamago, Chem. Rev. 2009, 109, 5051-5068.
34. S. Yamago, B. Ray, K. Iida, J. Yoshida, T. Tada, K. Yoshizawa, Y. Kwak, A. Goto, T. Fukuda, J. Am. Chem. Soc. 2004, 126, 13908-13909.
35. B. Ray, M. Kotani, S. Yamago, Macromolecules 2006, 39, 5259-5265.
36. S. Yamago, E. Kayahara, M. Kotani, B. Ray, Y. Kwak, A. Goto, T. Fukuda, Angew. Chem. 2007, 119, 1326-1328
37. Angew. Chem. Int. Ed. 2007, 46, 1304-1306.
38. E. Kayahara, S. Yamago, J. Am. Chem. Soc. 2009, 131, 2508-2513.
39. S. Yamago, T. Yamada, M. Togai, Y. Ukai, E. Kayahara, N. Pan, Chem. Eur. J. 2009, 15, 1018-1029.
40. T. Yamada, E. Mishima, K. Ueki, S. Yamago, Chem. Lett. 2008, 37, 650-651.
41. S. Yamago, E. Kayahara, H. Yamada, React. Funct. Polym. 2009, 69, 416-423.
42. V. Coessens, T. Pintauer, K. Matyjaszewski, Prog. Polym. Sci. 2001, 26, 337-377.
43. K. Matyjaszewski, Y. Gnanou, L. Leibler, Macromolecular Engineering: Precise Synthesis, Materials Properties, Applications, Wiley-VCH, Weinheim, 2007.
44. B. Boutevin, G. David, C. Boyer, Adv. Polym. Sci. 2007, 206, 31-135.
45. K. Matyjaszewski, N. V. Tsarevsky, Nat. Chem. 2009, 1, 276-288.
46. M. Destarac, Macromol. React. Eng. 2010, 4, 165-179.
47. S. Yamago, K. Iida, J. Yoshida, J. Am. Chem. Soc. 2002, 124, 13666-13667.
48. A. Goto, Y. Kwak, T. Fukuda, S. Yamago, K. Iida, M. Nakajima, J. Yoshida, J. Am. Chem. Soc. 2003, 125, 8720-8721.
49. S. Yamago, Synlett 2004, 1875-1890.
50. Y. Sugihara, Y. Kagawa, S. Yamago, M. Okubo, Macromolecules 2007, 40, 9208-9211.
51. S. Yusa, S. Yamago, M. Sugahara, S. Morikawa, T. Yamamoto, Y. Morishima, Macromolecules 2007, 40, 5907-5915.
52. E. Kayahara, S. Yamago, Y. Kwak, A. Gota, T. Fukuda, Macromolecules 2008, 41, 527-529.
53. J. Hasegawa, K. Kanamori, K. Nakanishi, T. Hanada, S. Yamago, Macromolecules 2009, 42, 1270-1277.
54. S. Yamago, Y. Ukai, A. Matsumoto, Y. Nakamura, J. Am. Chem. Soc. 2009, 131, 2100-2101.
55. N. Petragnani, H. A. Stefani, Tellurium in Organic Synthesis, 2 nd ed., Academic Press, London, 2007.
56. N. Petragnani, H. A. Stefani, Tetrahedron 2005, 61, 1613-1679.
57. J. o. V. Comasseto, A. A. Dos Santos, Phosphorus Sulfur Silicon Relat. Elem. 2008, 183, 939-947.
58. T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem. 1987, 99, 1221-1222
59. Angew. Chem. Int. Ed. Engl. 1987, 26, 1187-1188.
60. T. Hiiro, Y. Morita, T. Inoue, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Am. Chem. Soc. 1990, 112, 455-457.
61. T. Kanda, S. Kato, T. Sugino, N. Kambe, N. Sonoda, J. Organomet. Chem. 1994, 473, 71-83.
62. S. Yamago, K. Fujita, M. Miyoshi, M. Kotani, J. Yoshida, Org. Lett. 2005, 7, 909-911.
63. S. Yamago, K. Iida, J. Yoshida, J. Am. Chem. Soc. 2002, 124, 2874-2875.
64. M. Uchiyama, M. Koike, M. Kameda, Y. Kondo, T. Sakamoto, J. Am. Chem. Soc. 1996, 118, 8733-8734.
65. M. Uchiyama, Y. Kondo, T. Miura, T. Sakamoto, J. Am. Chem. Soc. 1997, 119, 12372-12373.
66. M. Uchiyama, M. Kameda, O. Mishima, N. Yokoyama, M. Koike, Y. Kondo, T. Sakamoto, J. Am. Chem. Soc. 1998, 120, 4934-4946.
67. M. Uchiyama, T. Furuyama, M. Kobayashi, Y. Matsumoto, K. Tanaka, J. Am. Chem. Soc. 2006, 128, 8404-8405.
68. T. Furuyama, M. Yonehara, S. Arimoto, M. Kobayashi, Y. Matsumoto, M. Uchiyama, Chem. Eur. J. 2008, 14, 10348-10356.
69. S. Nakamura, C.-Y. Liu, A. Muranaka, M. Uchiyama, Chem. Eur. J. 2009, 15, 5686-5694.
70. A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396-3399
71. Angew. Chem. Int. Ed. 2004, 43, 3333-3336.
72. H. Ila, O. Baron, A. J. Wagner, P. Knochel, Chem. Lett. 2006, 35, 2-7.
73. While we did not characterize the structure of the anion species, we tentatively call it a zincate enolate here.
74. M. JÃrgensen, S. Lee, X. Liu, J. P. Wolkowski, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 12557-12565.
75. H. L. Hsieh, R. P. Quirk, Anionic Polymerization: Principles and Practical Applications, Marcel Dekker, New York, 1996.
76. M. Janata, L. Lochmann, A. H. E. Müller, Makromol. Chem. 1990, 191, 2253-2260.
77. M. Janata, L. Lochmann, P. Vlček, J. Dybal, A. H. E. Müller, Makromol. Chem. 1992, 193, 101-112.
78. D. W. Cho, H.-Y. Lee, S. W. Oh, J. H. Choi, H. J. Park, P. S. Mariano, U. C. Yoon, J. Org. Chem. 2008, 73, 4539-4547.
79. J.-F. Lutz, H. G. Börner, Prog. Polym. Sci. 2008, 33, 1-39.
80. When benzaldehyde was added after the exchange reaction, the reaction gave a mixture of 3A and 2A with same composition, regardless of the starting substrates, due to the rapid equilibrium between the anionic and heteroatom compounds.
81. X. Chen, Y. Yamamoto, K.-Y. Akiba, Heteroat. Chem. 1995, 6, 293-303.
82. T. Kanda, S. Kato, N. Kambe, Y. Kohara, N. Sonoda, J. Phys. Org. Chem. 1996, 9, 29-34.