Abstract
An asymmetric oxidative cross-coupling polymerization with a binary catalyst system of an achiral or chiral copper complex and a Lewis acid was investigated. Both the copper and Lewis acid catalysts significantly affected the catalyst activity, cross-coupling and stereoselectivities during the polymerization. The polymerization of methyl 3,7-dihydroxynaphthalene-2-carboxylate using a copper(I)-bisoxazoline catalyst at room temperature under an O2 atmosphere in the presence of Yb(OTf)3 proceeded with a cross-coupling selectivity of 97%.
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References
J. M. Brunel, Chem. Rev., 105, 857 (2005).
M. Putala, Enantiomer, 4, 243 (1999).
M. Hovorka, J. Günterová, and J. Závada, Tetrahedron Lett., 31, 413 (1990).
M. Hovorka, R. Šcigel, J. Günterová, M. Tichý, and J. Závada, Tetrahedron, 48, 9503 (1992).
M. Smrcina, J. Poláková, Š. Vyskocil, and P. Kocovský, J. Org. Chem., 58, 4534 (1993).
M. Smrcina, Š. Vyskocil, B. Máca, M. Polášek, T. A. Claxton, A. P. Abbott, and P. Kocovský, J. Org. Chem., 59, 2156 (1994).
T. Temma and S. Habaue, Tetrahedron Lett., 46, 5655 (2005).
T. Temma, B. Hatano, and S. Habaue, Tetrahedron, 62, 8559 (2006).
S. Habaue, Y. Takahashi, and T. Temma, Tetrahedron Lett., 48, 7301 (2007).
P. Yan, Y. Sugiyama, Y. Takahashi, H. Kinemuchi, T. Temma, and S. Habaue, Tetrahedron, 64, 4325 (2008).
T. Temma and S. Habaue, J. Polym. Sci., Part A: Polym. Chem., 43, 6287 (2005).
T. Temma and S. Habaue, J. Polym. Sci., Part A: Polym. Chem., 46, 1034 (2008).
T. Temma, Y. Takahashi, Y. Yoshii, and S. Habaue, Polym. J., 39, 524 (2007).
T. Temma, B. Hatano, and S. Habaue, Polymer, 47, 1845 (2006).
L. Pu, Chem. Rev., 104, 1687 (2004).
L. Ma, P. S. White, and W. Lin, J. Org. Chem., 67, 7577 (2002).
A. K.-Y. Jen, Y. Liu, Q.-S. Hu, and L. Pu, Appl. Phys. Lett., 75, 3745 (1999).
M. Nakajima, I. Miyoshi, K. Kanayama, S. Hashimoto, M. Noji, and K. Koga, J. Org. Chem., 64, 2264 (1999).
X. Li, J. Yang, and M. C. Kozlowski, Org. Lett., 3, 1137 (2001).
J. Gao, J. H. Reibenspies, and A. E. Martell, Angew. Chem., Int. Ed., 42, 6008 (2003).
Y. Yamamoto, S. Onuki, M. Yumoto, and N. Asao, J. Am. Chem. Soc., 116, 421 (1994).
G. S. C. Srikanth and S. L. Castle, Tetrahedron Lett., 61, 10377 (2005).
J. Zimmerman and M. P. Sibi, Top. Curr. Chem., 263, 107 (2006).
C. L. Mero and N. A. Porter, J. Org. Chem., 65, 775 (2000).
H. Baraki, S. Habaue, and Y. Okamoto, Macromolecules, 34, 4724 (2001).
Y. Isobe, D. Fujioka, S. Habaue, and Y. Okamoto, J. Am. Chem. Soc., 123, 7180 (2001).
B. Ray, Y. Isobe, K. Morioka, S. Habaue, Y. Okamoto, M. Kamigaito, and M. Sawamoto, Macromolecules, 36, 543 (2003).
S. Habaue, T. Temma, Y. Sugiyama, and P. Yan, Tetrahedron Lett., 48, 8595 (2007).
S. R. Wyatt, Q.-S. Hu, X.-L. Yan, W. B. Bare, and L. Pu, Macromolecules, 34, 7983 (2001).
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Yan, P., Temma, T. & Habaue, S. Lewis-Acid-Assisted Highly Selective Oxidative Cross-Coupling Polymerization with Copper Catalysts. Polym J 40, 710–715 (2008). https://doi.org/10.1295/polymj.PJ2008052
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DOI: https://doi.org/10.1295/polymj.PJ2008052
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