Synthesis of Guanidines from Amines and Carbodiimides Catalyzed by Mono-Indenyl-Ligated Rare Earth Metal Bis(silylamide) Complexes
Jue Chen
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, China
Search for more papers by this authorYibin Wang
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, China
Search for more papers by this authorCorresponding Author
Yunjie Luo
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, China
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, ChinaSearch for more papers by this authorJue Chen
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, China
Search for more papers by this authorYibin Wang
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, China
Search for more papers by this authorCorresponding Author
Yunjie Luo
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, China
Organometallic Chemistry Laboratory, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, ChinaSearch for more papers by this authorAbstract
Nucleophilic addition of primary aromatic amines to carbodiimides in the presence of catalytic amount of the mono-indenyl-ligated rare earth metal bis(silylamide) complexes (C9H6CMe2CH2C5H4N-α)Ln[N(SiHMe2)2]2 at room temperature afforded efficiently a series of guanidines with a wide spectrum of substituents on the nitrogen atoms.
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REFERENCES
- 1a
Guanidines: Historical, Biological, Biochemical and Clinical Aspects of the Naturally Occurring Guanidino Compounds, Eds.: A. Mori; B. D. Cohen; A. Lowenthal, Plenum Press, New York, 1985.
10.1007/978-1-4757-0752-6 Google Scholar
- 1b Guanidines 2: Further Explorations of the Biological and Clinical Significance of Guanidino Compounds, Eds.: A. Mori; B. D. Cohen; H. Koide, Plenum Press, New York, 1987.
- 1c Hu, L.-Y.; Guo, J.; Magar, S. S.; Fischer, J. B.; Burke-Howise, K. J.; Durant, G. J.. J. Med. Chem., 1997, 40, 4281.
- 1d
Manimala, J. C.;
Anslyn, E. V..
Eur. J. Org. Chem.,
2002,
67,
3909.
10.1002/1099-0690(200212)2002:23<3909::AID-EJOC3909>3.0.CO;2-J Google Scholar
- 1e Trifonov, A. A.. Coord. Chem. Rev., 2010, 254, 1327.
- 1f Bailey, P. J.; Pace, S.. Coord. Chem. Rev., 2001, 214, 91.
- 2a Tin, M. K. T.; Thirupathi, N.; Yap, G. P. A.; Richeson, D. S.. J. Chem. Soc., Dalton Trans., 1999, 2947.
- 2b Tin, M. K. T.; Thirupathi, N.; Yap, G. P. A.; Richeson, D. S.. Inorg. Chem., 1998, 37, 6728.
- 3a Ong, T. G.; Yap, G. P. A.; Richeson, D. S.. J. Am. Chem. Soc., 2003, 125, 8100.
- 3b Montilla, F.; Pastor, A.; Galindo, A.. J. Organomet. Chem., 2004, 689, 993.
- 4a Ong, T. G.; O′Brien, J. S.; Korobkov, I.; Richeson, D. S.. Organometallics, 2006, 25, 4728.
- 4b Zhou, S. L.; Wang, S.; Yang, G.; Li, Q.; Zhang, L.; Yao, Z.; Zhou, Z.; Song, H.. Organometallics, 2007, 26, 3755.
- 4c Li, Q.; Wang, S.; Zhou, S.; Yang, G.; Zhu, X.; Liu, Y.. J. Org. Chem., 2007, 72, 6763.
- 4d Shen, H.; Chan, H. S.; Xie, Z. W.. Organometallics, 2006, 25, 5515.
- 5a Zhang, W.; Nishiura, M.; Hou, Z.. J. Am. Chem. Soc., 2005, 127, 16788.
- 5b Zhang, W.; Nishiura, M.; Hou, Z.. Synlett, 2006, 8, 1213.
- 5c Zhang, W.; Nishiura, M.; Hou, Z.. Chem. Eur. J., 2007, 13, 4037.
- 6 Alonso-Moreno, C.; Carrillo-Hermosilla, F.; Garcés, A.; Otero, A.; López-Solera, I.; Rodríguez, A. M.; Antinolo, A.. Organometallics, 2010, 29, 2789.
- 7 Zhang, W.-X.; Li, D.; Wang, Z.; Xi, Z.. Organometallics, 2009, 28, 882.
- 8 Li, D.; Guang, J.; Zhang, W.-X.; Wang, Y.; Xi, Z.. Org. Biomol. Chem., 2010, 8, 1816.
- 9a Luo, Y. J.; Lei, Y. L.; Fan, S. M.; Wang, Y. B.; Chen, J.. Dalton Trans., 2013, 42, 4040.
- 9b Wang, Y. B.; Lei, Y. L.; Chi, S. H.; Luo, Y. J.. Dalton Trans., 2013, 42, 1862.
- 9c Chen, F.; Fan, S. M.; Wang, Y. B.; Chen, J.; Luo, Y. J.. Organometallics, 2012, 31, 3730.
- 9d Wang, Y. B.; Luo, Y. J.; Chen, J.; Xue, H. M.; Liang, H. Z.. New J. Chem., 2012, 36, 933.
- 9e Luo, Y. J.; Feng, X. Y.; Wang, Y. B.; Fan, S. M.; Lei, Y. L.; Liang, H. Z.. Organometallics, 2011, 30, 3270.
- 9f Luo, Y. J.; Fan, S. M.; Yang, J. P.; Fang, J. H.; Xu, P.. Dalton Trans., 2011, 40, 3053.
- 10 Zhang, X. M.; Wang, C. Y.; Qian, C. W.; Han, F. B.; Xu, F.; Shen, Q.. Tetrahedron, 2011, 67, 8790.
- 11 Liu, C.; Zhou, S.; Wang, S.; Zhang, L.; Yang, G.. Dalton Trans., 2010, 39, 8994.
