Biaryl Coupling and Oxidation Reactions of Aromatic Alcohols Catalyzed by VO(acac)2

Chang-Ying Chu; Der-Ren  Hwang; Sheng-Kai Wang; Biing-Jiun Uang

doi:10.6180/jase.2003.6.2.01

Biaryl Coupling and Oxidation Reactions of Aromatic Alcohols Catalyzed by VO(acac)2

Chemistry / Biochemistry

Chang-Ying Chu¹, Der-Ren Hwang¹, Sheng-Kai Wang¹ and Biing-Jiun Uang ¹

¹Department of Chemistry National Tsing Hua University Hsinchu, Taiwan 300, R.O.C.

Received: February 10, 2003
Accepted: March 3, 2003
Publication Date: June 1, 2003

Download Citation: ||https://doi.org/10.6180/jase.2003.6.2.01

ABSTRACT

The biaryl coupling of substituted aromatic alcohols and the oxidation of p-hydroquinones with molecular oxygen catalyzed by VO(acac)₂ were achieved in good to excellent yields.

Keywords: Biaryl coupling, VO(acac)2, Oxidation, Aromatic Alcohols

REFERENCES

[1] Fukuyama, Y.; Asakawa, Y. J. Chem. Soc., Perkin Trans 1 1991, 2737.
[2] (a) Kobayashi, E.; Ando, K.; Nakano, H.; Tamaoki, T. J. Antibiot. 1989, 42, 153. (b) Kobayashi, E.; Nakano, H.; Morimoto, M.; Tamaoki, T. Biochem. Biophys. Res. Commun. 1989, 159, 548.
[3] Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426.
[4] Corridi, H.; Hardegger, E. Helv. Chem. Acta. 1955, 38, 2030.
[5] Boyd, M. R.; Hallock, Y. F.; Cardellina, J. H.; Manfredi, K. P.; Blunt, J. W.; McMohan, J. B.; Buckheit, R. W.; Bringmann, G.; Schaffer, M.; Cragg, G. M.; Thomas, D. W.; Jato, J. G. J. Med. Chem. 1994, 37, 1740.
[6] (a) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1991, 503. (b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1021. (c) Pu, L. Chem. Rev. 1998, 98, 2405.
[7] (a) Kametani, T.; Fukumoto, K. Synthesis 1972, 657. (b) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331.
[8] (a) Toda, F.; Takana, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007. (b) Pummerer, R.; Prell, E.; Rieche, A. Ber. 1926, 59, 2159. (c) Feringa, B.; Wynberg, H. J. Org. Chem. 1981, 46, 2547.
[9] (a) Dewar, M. J. S.; Nakaya, T. J. Am. Chem. Soc. 1968, 90, 7134. (b) Yamamoto, K.; Fukushima, H.; Okamoto, Y.; Hatada, K.; Nakajaki, M. J. Chem. Soc., Chem. Commun. 1984, 1111.
[10] (a) Feringa, B.; Wynberg, H. Tetrahedron Lett. 1977, 18, 4447. (b) Brussee, J.; Groendijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313. (c) Smrcina, M.; Polakova, J.; Vyskocil, S.; Kocovsky, P. J. Org. Chem. 1993, 58, 4534.
[11] Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
[12] Sakamoto, T.; Yonehara, H.; Pac, C. J. Org. Chem. 1994, 59, 6859.
[13] (a) Hirao, T. J. Inorg. Biochem. 2000, 80, 27. (b) Hirao, T. Chem. Rev. 1997, 97, 2707. (c) Dalko, P. I. Tetrahedron 1995, 51, 7579. (d) Hirao, T.; Fujii, T.; Tanaka, T.; Ohshiro, Y.; Ikada, I. J. Synth. Org. Chem. Jpn. 1994, 52, 197. (e) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (f) Pons, J.-M.; Santelli, M. Tetrahedron 1988, 44, 4295. (g) Freeman F. Organic Syntheses by Oxidation with Metal Compounds, W. J. Mijs, C. R. H. I. de Jonge (Eds.), Plenum: NY, U.S.A., 1986; Chapter 1. (h) Sheldon, R. A.; Kochi, J. K. Metal Catalyzed Oxidations of Organic Compounds, Academic: NY, U.S.A., 1981. (i) Ho, T.-L. Synthesis 1979, 1. (j) Schrock, R. R.; Parshall, G. W. Chem. Rev. 1976, 76, 243.
[14] Kupchan, S. M.; Liepa, A. J.; Kameswaran, V.; Bryan, R. F. J. Am. Chem. Soc. 1973, 95, 6861.
[15] Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919.
[16] Nakajima, K.; Kojima, K.; Kojima, M.; Fujita, J. Bull. Chem. Soc. Jpn. 1990, 63, 2620.
[17] Hwang, D.-R.; Chen, C.-P.; Uang, B.-J. Chem. Commun. 1999, 1207.
[18] Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 3, 463.
[19] Tatsuno, Y.; Tatsuda, M.; Otsuka, S. J. Chem. Soc., Chem. Commun. 1982, 1100.
[20] Hwang, D.-R.; Chu, C.-Y.; Wang, S.-K.; Uang, B.-J. Synlett. 1999, 77.
[21] (a) Yamamoto, K.; Oyaizu, K.; Iwasaki, N.; Tsuchida, E. Chem. Lett. 1993, 1223. (b) Yamamoto, K.; Tsuchida, E.; Nishide, H.; Jikei, M.; Oyaizu, K. Macromolecules 1993, 26, 3432.
[22] (a) Wang, Y.; Sun, J.; Ding, K. Tetrahedron 2000, 56, 4447. (b) Sakamoto, T.; Yonehara, H.; Pac, C. J. Org. Chem. 1994, 59, 6859. (c) Dean, F. A.; Herbin, G. A.; Matkin, D. A.; Price, A. W.; Robinson M. L. J. Chem. Soc., Perkin Trans. 1 1980, 1986. (d) Armstrong, D. R.; Cameron, C.; Nonhebel, D. C.; Perkins, P. G. J. Chem. Soc., Perkin Trans. 2 1983, 581. (e) Pratt, D. V.; Ruan, F.; Hopkins, P. B. J. Org. Chem. 1987, 52, 5053. (f) Bosch, E.; Rathore, R.; Kochi, J. K. J. Org. Chem. 1994, 59, 2529. (g) Takaki, K.; Shimasaki, Y.; Shishido, T.; Takehira, K. Bull. Chem. Soc. Jpn. 2002, 75, 311. (h) Barton, D. H. R.; Sas, W. Tetrahedron 1990, 46, 3419. (i) Singh, P. K.; Rohtagi, B. K.; Khanna, R. N. Synth. Commun. 1992, 22, 987. (j) Perez, J. M.; Lopez-Alvarado, P.; Avendano, C.; Menendez, J. C. Tetrahedron 2000, 56, 1561. (k) Grennberg, H.; Gogoll, A.; Baeckwall, J.-E. J. Org. Chem. 1991, 56, 5808.