Iron(III) Chloride Catalyzed Oxidative Coupling Reaction of 1,2-Diarylethylene Derivatives
Derong Ji
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorLidan Su
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorKeqing Zhao
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorBiqin Wang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorPing Hu
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorChun Feng
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorShikai Xiang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorCorresponding Author
Hua Yang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China, Tel.: 0086-028-84760802Search for more papers by this authorCorresponding Author
Chenggang Zhang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China, Tel.: 0086-028-84760802Search for more papers by this authorDerong Ji
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorLidan Su
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorKeqing Zhao
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorBiqin Wang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorPing Hu
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorChun Feng
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorShikai Xiang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
Search for more papers by this authorCorresponding Author
Hua Yang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China, Tel.: 0086-028-84760802Search for more papers by this authorCorresponding Author
Chenggang Zhang
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China
College of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610066, China, Tel.: 0086-028-84760802Search for more papers by this authorAbstract
A nontoxic FeCl3 catalyzed intramolecular oxidative coupling reaction was developed for mild synthesis of a series of phenanthrenes with different substituents. The method involves cross dehydrogenative coupling of a variety of 1,2-diarylethylene derivatives with di-tert-butylperoxide (DTBP) as a sole oxidant at room temperature in CH2Cl2/TFA (9:1 V/V) to yield phenanthrenes in good to excellent yields.
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REFERENCES
- 1a Suzanne, C. B.; Eric, J. H.; Emil, L.; Paul, J. C.. Organometallics, 2005, 24, 5518.
- 1b Carina, G.; Fabio, D.. J. Org. Chem., 2008, 73, 5379.
- 1c Reuben, H.; Antoine, R.; Ciprian, M. C.; Kylie, L. L.; Audrey, M.. Chem. Commun., 2012, 48, 3360.
- 2 Marcelo, R. D. S.; Alexandre, F. G.; Fabio, C. G.; Paulo, A. Z. S.; Brenno, A. D. N.. ChemSusChem., 2012, 5, 2383.
- 3 Marcelo, R. D. S.; Julia, R. D.; Aline, M. A.; Alexandre, F. G.; Fabio, C. G.; Silvia, M. T.; Alexandre, L. P.; Paulo, A. Z. S.; Brenno, A. D. N.. ChemSusChem., 2012, 5, 716.
- 4 Correa, A.; Bolm, C.. Angew. Chem., Int. Ed., 2007, 46, 8862.
- 5
Bistri, O.;
Correa, A.;
Bolm, C..
Angew. Chem., Int. Ed.,
2008,
120,
596.
10.1002/ange.200704018 Google Scholar
- 6 Bolm, C.; Legros, J.; Paih, J. L.; Zani, L.. Chem. Rev., 2004, 104, 6217.
- 7 Correa, A.; Mancheno, O. G.; Bolm, C.. Chem. Soc. Rev., 2008, 37, 1108.
- 8 Guo, X. W.; Li, Z. P.; Li, C. J.. Chemistry, 2012, 22, 1434.
- 9 Li, Z. G.; Jin, Z.; Huang, R. Q.. Synthesis, 2001, 16, 2365.
- 10 Chemler, S. R.. Curr. Bioact. Compd., 2009, 5, 2.
- 11a Kim, S.; Lee, T.; Lee, E.; Lee, J.; Fan, G.; Lee, S.; Kim, D.. J. Org. Chem., 2004, 69, 3144.
- 11b Camacho-Davila, A.; Herndon, J. W.. J. Org. Chem., 2006, 71, 6682.
- 11c Ihara, M.. Chem. Pharm. Bull., 2006, 54, 765.
- 11d Kim, S.; Lee, Y.; Lee, M.; Lee, J.; Fu, T.; Song, Y.; Cho, Y.; Kim, J. D.. J. Org. Chem., 2007, 72, 4886.
- 12a Li, Z. P.; Li, C. J.. J. Am. Chem. Soc., 2004, 126, 11810.
- 12b Daugulis, O.; Zaitsev, V. G.. Angew. Chem., Int. Ed., 2005, 44, 4046.
- 12c Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K.. J. Am. Chem. Soc., 2006, 128, 8754.
- 12d Liu, W.; Cao, H.; Lei, A. W.. Angew. Chem., 2010, 122, 2048.
- 13a Halton, B.; Maidment, A. I.; Officer, D. L.; Warner, J. M.. Aust. J. Chem., 1984, 37, 2119.
- 13b Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.. J. Am. Chem. Soc., 1993, 115, 6426.
- 13c Li, H.; Hu, T. S.; Wang, K. L.; Liu, Y. X.; Fan, Z. J.; Huang, R. Q.; Wang, Q. M.. Lett. Org. Chem., 2006, 3, 806.
- 14a Taylor, E. C.; Andrade, J. G.; Rall, G. J. H.; Mckillop, A.. J. Am. Chem. Soc., 1980, 102, 6513.
- 14b Mckillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C.. J. Am. Chem. Soc., 1980, 102, 6504.
- 14c Bringmann, G.; Walter, R.; Weirich, R.. Angew. Chem., Int. Ed. Engl., 1990, 29, 977.
- 15 Feldman, K. S.; Ensel, S. M.. J. Am. Chem. Soc., 1994, 116, 3357.
- 16a Jin, Z.; Wang, Q. M.; Huang, R. Q.. Synth. Commun., 2004, 34, 119.
- 16b Wang, K. L.; Lu, M. Y.; Wang, Q. M.; Huang, R. Q.. Tetrahedron, 2008, 64, 7504.
- 17a Bolm, C.; Legros, J.; Paih, J. L.; Zani, L.. Chem. Rev., 2004, 104, 6217.
- 17b Sarhan, A. A. O.; Bolm, C.. Chem. Soc. Rev., 2009, 38, 2730.
- 18 Lu, M. Y.; Wang, K. L.; Cai, F.; Wang, H. Y.; Wang, Q. M.. Chin. J. Chem., 2008, 26, 2241.
- 19a Wang, K. L.; Lu, M. Y.; Yu, A.; Zhu, X. Q.; Wang, Q. M.. J. Org. Chem., 2009, 74, 935.
- 19b Wang, K. L.; Hu, Y. N.; Wu, M.; Li, Z.; Lu, Z. H.; Su, B.; Yu, A.; Liu, Y.; Wang, Q. M.. Tetrahedron, 2010, 66, 9135.
- 19c Su, B.; Li, L.; Hu, Y. N.; Liu, Y. X.; Wang, Q. M.. Adv. Synth. Catal., 2012, 354, 383.
- 20 Baker, D. C.; Chen, Y. C.; Zhong, S. B.. WO 03070166 Chem. Abstar., 2003, 139, 214611.
- 21 Halton, B.; Maidment, A. I.; Officer, D. L.; Warner, J. M.. Aust. J. Chem., 1984, 37, 2119.
- 22 Ji, D. R.; Su, L. D.; Zhang, C. G.. Chin. J. Org. Chem., 2012, 32, 2334.
- 23 Wang, Z. W.; Wu, M.; Wang, Y.; Li, Z.; Wang, L.; Han, G. F.; Chen, F. Z.; Liu, Y. X.; Wang, K. L.; Zhang, A.; Meng, L. H.; Wang, Q. M.. Eur. J. Med. Chem., 2012, 51, 250.
- 24 Bremmer, M. L.; Khatri, N. A.; Weinreb, S. M.. J. Org. Chem., 1983, 48, 3661.
- 25 Stomberg, R.. Acta Cryst., 1995, 51, 2698.
- 26 Tobinaga, S.. Bioorg. Chem., 1975, 4, 110.
- 27 Buckley, T. F.; Henry, R.. J. Org. Chem., 1983, 48, 4222.
- 28 Marchin, P.; Belleau, B.. Can. J. Chem., 1958, 36, 581.
- 29 Li, J. J., M.S. Thesis, Sichuan Normal University, Chengdu, 2010, pp. 26−33 (in Chinese).