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Evaluation of Nitroxide Radical Catalyst Activity in C-H Activation Step of the Oxidative Coupling between 9,10-Dihydroacridine and Nitromethane
Corresponding Author(s) : Hiroaki Gotoh
Asian Journal of Chemistry,
Vol. 31 No. 9 (2019): Vol 31 Issue 9
Abstract
Organocatalysts have been the subject of intense research effort because of their low toxicity, facile handling, and eco-friendly characteristics. Recently, the development of C-H activation reaction using organocatalysts has also been studied. Herein, we report the studies on the oxidative coupling of 9,10-dihydroacridine and nitromethane using a series of stable radicals. tert-Butyl(10-phenyl-9-anthryl)nitroxide was found to be an optimal catalyst for the coupling reaction.
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- C.-J. Li, Acc. Chem. Res., 42, 335 (2009); https://doi.org/10.1021/ar800164n.
- L. Tebben and A. Studer, Angew. Chem. Int. Ed., 50, 5034 (2011); https://doi.org/10.1002/anie.201002547.
- B. Zhang, Y. Cui and N. Jiao, Chem. Commun., 48, 4498 (2012); https://doi.org/10.1039/c2cc30684k.
- B. Han, C. Wang, R.F. Han, W. Yu, X.Y. Duan, R. Fang and X.L. Yang, Chem. Commun., 47, 7818 (2011); https://doi.org/10.1039/c1cc12308d.
- W. Hu, J.P. Lin, L.R. Song and Y.Q. Long, Org. Lett., 17, 1268 (2015).
- R. Ding, J.-G. Fu, G.-Q. Xu, B.-F. Sun and G.-Q. Lin, J. Org. Chem., 79, 240 (2014); https://doi.org/10.1021/jo402419h.
- C. Galli, P. Gentili and O. Lanzalunga, Angew. Chem. Int. Ed., 47, 4790 (2008); https://doi.org/10.1002/anie.200704292.
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- J. Chang, K. Zhao and S. Pan, Tetrahedron Lett., 43, 951 (2002); https://doi.org/10.1016/S0040-4039(01)02302-4.
- Á. Pintér, A. Sud, D. Sureshkumar and M. Klussmann, Angew. Chem. Int. Ed., 49, 5004 (2010); https://doi.org/10.1002/anie.201000711.
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- Y.-X. Chen, L.-F. Qian, W. Zhang and B. Han, Angew. Chem. Int. Ed., 47, 9330 (2008); https://doi.org/10.1002/anie.200803381.
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- K.-U. Schoening, Chim. Oggi, 28, 18 (2010).
- Q. Cao, L.M. Dornan, L. Rogan, N.L. Hughes and M.J. Muldoon, Chem. Commun., 50, 4524 (2014); https://doi.org/10.1039/C3CC47081D.
- M.S. Maji, T. Pfeifer and A. Studer, Angew. Chem. Int. Ed., 47, 9547 (2008); https://doi.org/10.1002/anie.200804197.
- M. Shibuya, M. Tomizawa, I. Suzuki and Y. Iwabuchi, J. Am. Chem. Soc., 128, 8412 (2006); https://doi.org/10.1021/ja0620336.
- T. Sonobe, K. Oisaki and M. Kanai, Chem. Sci., 3, 3249 (2012); https://doi.org/10.1039/c2sc20699d.
- R. Toba, H. Gotoh and K. Sakakibara, Org. Lett., 16, 3868 (2014); https://doi.org/10.1021/ol501328k.
- E.F. Ullman, J.H. Osiecki, D.G.B. Boocock and R. Darcy, J. Am. Chem. Soc., 94, 7049 (1972); https://doi.org/10.1021/ja00775a031.
- M.B. Neiman, Y.G. Mamedova and E.G. Rozantsev, Azerbaidzhanskii Khimicheskii Zhurnal, 6, 37 (1962).
- E.G. Rozantzev and L.A. Krinitzkaya, Tetrahedron, 21, 491 (1965); https://doi.org/10.1016/S0040-4020(01)82219-5.
- H. Zimmer, D.C. Lankin and S.W. Horgan, Chem. Rev., 71, 229 (1971); https://doi.org/10.1021/cr60270a005.
- P. Ionita, Chem. Pap., 59, 11 (2005).
- M.S. Kharasch and B.S. Joshi, J. Org. Chem., 22, 1435 (1957); https://doi.org/10.1021/jo01362a033.
References
C.-J. Li, Acc. Chem. Res., 42, 335 (2009); https://doi.org/10.1021/ar800164n.
L. Tebben and A. Studer, Angew. Chem. Int. Ed., 50, 5034 (2011); https://doi.org/10.1002/anie.201002547.
B. Zhang, Y. Cui and N. Jiao, Chem. Commun., 48, 4498 (2012); https://doi.org/10.1039/c2cc30684k.
B. Han, C. Wang, R.F. Han, W. Yu, X.Y. Duan, R. Fang and X.L. Yang, Chem. Commun., 47, 7818 (2011); https://doi.org/10.1039/c1cc12308d.
W. Hu, J.P. Lin, L.R. Song and Y.Q. Long, Org. Lett., 17, 1268 (2015).
R. Ding, J.-G. Fu, G.-Q. Xu, B.-F. Sun and G.-Q. Lin, J. Org. Chem., 79, 240 (2014); https://doi.org/10.1021/jo402419h.
C. Galli, P. Gentili and O. Lanzalunga, Angew. Chem. Int. Ed., 47, 4790 (2008); https://doi.org/10.1002/anie.200704292.
O. Garcia Mancheno and T. Stopka, Synthesis, 45, 1602 (2013); https://doi.org/10.1055/s-0033-1338480.
Z.-L. Wang, X.-L. An, L.-S. Ge, J.-H. Jin, X. Luo and W.-P. Deng, Tetrahedron, 70, 3788 (2014); https://doi.org/10.1016/j.tet.2014.04.021.
J. Chang, K. Zhao and S. Pan, Tetrahedron Lett., 43, 951 (2002); https://doi.org/10.1016/S0040-4039(01)02302-4.
Á. Pintér, A. Sud, D. Sureshkumar and M. Klussmann, Angew. Chem. Int. Ed., 49, 5004 (2010); https://doi.org/10.1002/anie.201000711.
Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama and Y. Nishiyama, J. Org. Chem., 60, 3934 (1995); https://doi.org/10.1021/jo00118a002.
Y.-X. Chen, L.-F. Qian, W. Zhang and B. Han, Angew. Chem. Int. Ed., 47, 9330 (2008); https://doi.org/10.1002/anie.200803381.
W.-B. Qin, Q. Chang, Y.-H. Bao, N. Wang, Z.-W. Chen and L.-X. Liu, Org. Biomol. Chem., 10, 8814 (2012); https://doi.org/10.1039/c2ob26390d.
K.-U. Schoening, Chim. Oggi, 28, 18 (2010).
Q. Cao, L.M. Dornan, L. Rogan, N.L. Hughes and M.J. Muldoon, Chem. Commun., 50, 4524 (2014); https://doi.org/10.1039/C3CC47081D.
M.S. Maji, T. Pfeifer and A. Studer, Angew. Chem. Int. Ed., 47, 9547 (2008); https://doi.org/10.1002/anie.200804197.
M. Shibuya, M. Tomizawa, I. Suzuki and Y. Iwabuchi, J. Am. Chem. Soc., 128, 8412 (2006); https://doi.org/10.1021/ja0620336.
T. Sonobe, K. Oisaki and M. Kanai, Chem. Sci., 3, 3249 (2012); https://doi.org/10.1039/c2sc20699d.
R. Toba, H. Gotoh and K. Sakakibara, Org. Lett., 16, 3868 (2014); https://doi.org/10.1021/ol501328k.
E.F. Ullman, J.H. Osiecki, D.G.B. Boocock and R. Darcy, J. Am. Chem. Soc., 94, 7049 (1972); https://doi.org/10.1021/ja00775a031.
M.B. Neiman, Y.G. Mamedova and E.G. Rozantsev, Azerbaidzhanskii Khimicheskii Zhurnal, 6, 37 (1962).
E.G. Rozantzev and L.A. Krinitzkaya, Tetrahedron, 21, 491 (1965); https://doi.org/10.1016/S0040-4020(01)82219-5.
H. Zimmer, D.C. Lankin and S.W. Horgan, Chem. Rev., 71, 229 (1971); https://doi.org/10.1021/cr60270a005.
P. Ionita, Chem. Pap., 59, 11 (2005).
M.S. Kharasch and B.S. Joshi, J. Org. Chem., 22, 1435 (1957); https://doi.org/10.1021/jo01362a033.