Homocoupling of Aryl Bromides Catalyzed by Nickel Chloride in Pyridine
Xiao-Chun Tao
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorWei Zhou
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorYue-Ping Zhang
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorChun-Ya Dai
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorDong Shen
Project supported by the Ministry of Education of China.
Tel.: 0086-021-64252320
Search for more papers by this authorMei Huang
Laboratory of Chemical Physics, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorXiao-Chun Tao
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorWei Zhou
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorYue-Ping Zhang
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorChun-Ya Dai
Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorDong Shen
Project supported by the Ministry of Education of China.
Tel.: 0086-021-64252320
Search for more papers by this authorMei Huang
Laboratory of Chemical Physics, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorProject supported by the Ministry of Education of China.
Tel.: 0086-021-64252320
Abstract
Pyridine was used as a solvent for homocoupling of aryl bromides catalyzed by nickel chloride/triarylphosphine in the presence of zinc and recycled easily. Triphenylphosphine was the best ligand for nickel in this coupling reaction.
REFERENCES
- 1 Hassan, J.; Sevignon, M. C.; Gozzi, E.; Schulz, M.; Lemaire, M.. Chem. Rev., 2002, 102, 1359.
- 2a Yamamoto, T.; Maruyama, T.; Zhou, Z.; Ito, T.; Fukada, T.; Yomeda, Y.; Begum, F.; Ikeda, T.; Sasaki, S.; Takezoe, H.; Fukada, A.; Kubota, K.. J. Am. Chem. Soc., 1994, 116, 4832.
- 2b Schulz, E.; Fahmi, K.; Lemaire, M.. Acros Org. Acta, 1995, 1, 10.
- 2c Zhu, S.; Swager, T. M.. Adv. Mater., 1996, 8, 497.
- 2d Papilon, J.; Shulz, E.; Gélinas, S.; Lessard, J.; Lemaire, M.. Synth. Met., 1998, 96, 155.
- 3 Noyori, R.. Chem. Soc. Rev., 1989, 18, 187.
- 4a Bringmann, G.; Walter, R.; Weirich, R.. Angew. Chem., Int. Ed. Engl., 1990, 29, 977.
- 4b
Lehn, J. M., Supramolecular Chemistry, VCH, Weinheim, 1995.
10.1002/3527607439 Google Scholar
- 5a Miyaura, N.; Yangi, T.; Suzuki, A.. Synth. Commun., 1981, 11, 513.
- 5b Miyaura, N.; Suzuki, A.. Chem. Rev., 1995, 95, 2457.
- 5c Basu, B.; Das, P.; Bhuiyan, M. M. H.; Jha, S.. Tetrahedron Lett., 2003, 44, 3817.
- 6 Wallow, T. I.; Norak, B. M.. J. Org. Chem., 1994, 59, 5034.
- 7 Miller, J. A.; Farrell, R. P.. Tetrahedron Lett., 1998, 39, 6441.
- 8 Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y.. J. Am. Chem. Soc., 1988, 110, 8153.
- 9a Semmelhack, M. F.; Helquist, P. M.; Jones, L. D.. J. Am. Chem. Soc., 1971, 93, 5908.
- 9b Semmelhack, M. F.; Speltz, R. L.. J. Am. Chem. Soc., 1975, 97, 3873.
- 9c Semmelhack, M. F.; Helquist, P.; Jones, L. D.; Keller, L.; Mendelson, L.; Speltz, R. L.; Gorszynski, S. J.; Staufer, R. D.. J. Am. Chem. Soc., 1981, 103, 6460.
- 10 Kende, A. S.; Liebeskind, L.; Braitsch, D. M.. Tetrahedron Lett., 1975, 3375.
- 11
Zembayashi, M.;
Tamao, K.;
Yoshida, J.;
Kumada, M..
Tetrahedron Lett.,
1977,
47,
4089.
10.1016/S0040-4039(01)83434-1 Google Scholar
- 12 Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M.. Bull. Chem. Soc. Jpn., 1990, 63, 80.
- 13 Colon, I.; Kelsey, R. D.. J. Org. Chem., 1986, 51, 2627.
- 14a Gao, C.; Tao, X.; Qian, Y.; Huang, J.. Chem. Commun., 2003, 1444.
- 14b Gao, C.; Tao, X.; Qian, Y.; Huang, J.. Synlett, 2003, 11, 1716.
- 14c Tao, X.; Zhao, Y.; Shen, D.. Synlett, 2004, 359.
- 15 Bass, P.; Purdon, R. A.; Patterson, M. A. D.; Butler, E.. J. Pharmacol. Exp. Ther., 1966, 152, 104.
- 16 Krumholz, P.. J. Am. Chem. Soc., 1951, 73, 3487.
- 17 Brugget, P. A.; Graetzel, M.. J. Am. Chem. Soc., 1980, 102, 2461.
- 18 Christian, K.; Alexander, K.; Mir, W. H.. Chem. Rev., 2000, 100, 3553.
- 19 Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M.. Synthesis, 1984, 736.
- 20 Vanderesse, R.; Lourak, M.; Fort, Y.; Caubere, P.. Tetrahedron Lett., 1986, 27, 5483.
- 21 Fort, Y.; Becker, S.; Caubere, P.. Tetrahedron, 1994, 50, 11893.
- 22 Lin, G.; Hong, R.. J. Org. Chem., 2001, 66, 2877.
- 23 Qian, Y.; Wang, C.; Tao, X.; Huang, J.. Chin. J. Org. Chem., 2003, 23, 1264 (in Chinese).
- 24
Zincke, T..
Chem. Ber.,
1871,
4,
396.
10.1002/cber.187100401133 Google Scholar
- 25 Abiraj, K.; Srinivasa, G.; Channe, G. D.. Tetrahedron Lett., 2004, 45, 2081.
- 26 Jutand, A.; Mosleh, A.. J. Org. Chem., 1997, 45, 261.
- 27 Larock, R. C.; Bernhardt, J. C.. J. Org. Chem., 1977, 42, 1680.
