Ruthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors
Yuxiao Liu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorNa Yang
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorChanghu Chu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorCorresponding Author
Renhua Liu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, ChinaSearch for more papers by this authorYuxiao Liu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorNa Yang
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorChanghu Chu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorCorresponding Author
Renhua Liu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, ChinaSearch for more papers by this authorAbstract
An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
cjoc_201500325_sm_suppl.pdf255.7 KB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1a Corsaro, A.; Chiacchio, M. A.; Pistara, V.. Curr. Org. Chem., 2009, 13, 482.
- 1b Sandler, S. R.; Karo, W.. In Organic Functional Group Preparations, Academic Press, London, 1989.
- 2a
Greene, T. W.;
Wuts, P. G. M..
Protective Groups in Organic Synthesis, 3rd ed., John Wiley, New York, 1999.
10.1002/0471220574 Google Scholar
- 2b Zhao, W. C.; Sha, Y. W.. Chin. J. Org. Chem., 1996, 16, 121.
- 3 Shriner, R. L.; Fuson, R. C.; Curtin, D. Y.; Morrill, T. C., The Systematic Identification of Organic Compounds, 6th ed., John Wiley, New York, 1980.
- 4a Kim, Y. H.; Jung, J. C.; Kim, K. S.. Chem. Ind., 1992, 31.
- 4b Shinada, T.; Yoshihara, K.. Tetrahedron Lett., 1995, 36, 6701.
- 5a Ganboa, I.; Palomo, C.. Synth. Commun., 1983, 13, 941.
- 5b Ghiaci, M.; Hassan, I. G.. Synth. Commun., 1998, 28, 2275.
- 6a Shen, J. X.; Sun, J. K.; Qin, S. S.; Chu, C. H.; Liu, R. H.. Chin. J. Chem., 2014, 32, 405.
- 6b Wang, K.; Qian, X.; Cui, J.. Tetrahedron, 2009, 65, 10377.
- 6c Domingo, L. R.; Picher, M. T.; Arroyo, P.; Sez, J. A.. J. Org. Chem., 2006, 71, 9319.
- 6d Czekelius, C.; Carreira, E. M.. Angew. Chem., Int. Ed., 2005, 44, 612.
- 6e Kabalka, G. W.; Pace, R. D.; Wadgaonkar, P. P.. Synth. Commun., 1990, 20, 2453.
- 6f Baran, J.; Mayr, H.. J. Org. Chem., 1989, 54, 5012.
- 7a Lin, M. H.; Lin, L. Z.; Chuang, T. H.; Liu, H. J.. Tetrahedron, 2012, 68, 2630.
- 7b Li, J. T.; Meng, X. T.; Liu, L.; Chen, G.. Chin. J. Org. Chem., 2011, 31, 733.
- 7c Gogoi, P.; Hazarika, P.; Konwar, D.. J. Org. Chem., 2005, 70, 1934.
- 7d Bhar, S.; Guha, S.. Synth. Commun., 2005, 35, 1183.
- 7e De, S. K.. Tetrahedron Lett., 2003, 44, 9055.
- 7f Shirini, F.; Zolfigol, M. A.; Safari, A.; Mirjalili, B. F.. Tetrahedron Lett., 2003, 44, 7463.
- 7g Shirini, F.; Zolfigol, M. A.; Mallakpour, B.; Mallakpour, S. E.; Hajipour, A. R.; Baltork, I. M.. Tetrahedron Lett., 2002, 43, 1555.
- 7h Lee, S. Y.; Lee, B. S.; Lee, C. W.; Oh, D. Y.. J. Org. Chem., 2000, 65, 256.
- 8a Majireck, M. M.; Witek, J. A.; Weinreb, S. M.. Tetrahedron Lett., 2010, 51, 3555.
- 8b Martin, M.; Martinez, G.; Urpi, F.; Vilarrasa, J.. Tetrahedron Lett., 2004, 45, 5559.
- 8c Amold, J. N.; Hayes, P. Q.; Kohaus, R. L.; Mohan, R. S.. Tetrahedron Lett., 2003, 44, 9173.
- 8d Lukin, K. A.; Narayanan, B. A.. Tetrahedron, 2002, 58, 215.
- 9a Zhang, G. F.; Wen, X.; Ding, C. R.; Cao, X. J.. RSC Adv., 2013, 3, 22918.
- 9b Zhang, G. F.; Wen, X.. J. Org. Chem., 2011, 76, 4665.
- 9c Zhou, X. T.; Yuan, Q. L.; Ji, H. B.. Tetrahedron Lett., 2010, 51, 613.
- 9d Zhou, X. T.; Yuan, Q. L.; Ji, H. B.. Tetrahedron Lett., 2010, 51, 613.
- 9e Shaabani, A.; Farhangi, E.. Appl. Catal., 2009, 371, 148.
- 9f Bahrami, K.; Khodaei, M. M.; Gorgin, U.. Chin. J. Chem., 2009, 27, 384.
- 9g Gogoi, P.; Hazarika, P.; Konwar, D.. J. Org. Chem., 2005, 70, 1934.
- 9h Kanta, D. S.. Synth. Commun., 2004, 34, 4409.
- 10a Li, D. M.; Deng, Y. Q.. Tetrahedron Lett., 2004, 45, 265.
- 10b Maynez, S. R.; Pelavin, L.; Erker, G.. J. Org. Chem., 1975, 40, 3302.
- 10c DePuy, C. H.; Ponder, B. W., J. Am. Chem. Soc., 1959, 81, 4629.
- 11 Lin, M. H.; Liu, H. J.; Chang, C. Y.; Lin, W. C.; Chuang, T. H.. Molecules, 2012, 17, 2464.
- 12 Na, Q.; Shi, X. X.. Synlett, 2011, 7, 1028.
- 13 Chavan, S. P.; Soni, P.. Tetrahedron Lett., 2004, 45, 3161.
- 14a Jin, X. K.; Liu, Y. X.; Lu, Q. Q.; Liu, R. H.. Org. Biomol. Chem., 2013, 11, 3776.
- 14b Zhang, J. W.; Jiang, Q. Q.; Yang, D. J.; Zhao, X. M.; Dong, Y. L.; Liu, R. H.. Chem. Sci., 2015, DOI: 10.1039/C5SC01044F.
- 15 Sandler, S. R., Organic Functional Group Preparations, Academic Press, New York, 1968.