ZrCl4 as an Efficient Catalyst for Selective Tosylation of Alcohols with p-Toluenesulfonic Acid Tosylation of alcohols has directly been carried out with p-toluenesulfonic acid in methylene chloride under reflux using ZrCl4 as a catalyst. Primary alcohols were found to be tosylated chemoselectively over secondary alcohols
Chemistry Letters
Vol. 33 (2004) , No. 11 p.1428
ZrCl4 as an Efficient Catalyst for Selective Tosylation of Alcohols with p-Toluenesulfonic Acid
Biswanath Das and Vtukuri Saidi Reddy
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References
1) Part 54 in the series, “Studies on Novel Synthetic Methodologies.”
2) T. W. Greene and P. G. M. Wuts, “Protecting Groups in Organic Synthesis,” 3rd ed., Wiley, New York (1999).
3) a) G. W. Kabalka, M. Varma, R. S. Varma, P. C. Srivastava, and F. F. Knapp, Jr., J. Org. Chem., 51, 2386 (1986).
b) J. Hartung, S. Honig, R. Kneuer, and H. Wenner, Synthesis, 1997, 1433.
c) Y. Yoshida, Y. Sakakura, N. Aso, S. Okada, and Y. Tanabe, Tetrahedron, 55, 2183 (1999).
d) Y. Yoshida, K. Shimomishi, Y. Sakakura, S. Okada, N. Aso, and Y. Tanabe, Synthesis, 1999, 1633.
4) Y. Nitta and Y. Arakawa, Chem. Pharm. Bull., 33, 1380 (1985).
5) a) B. M. Choudary, N. S. Chowdari, and M. L. Kantam, Tetrahedron, 56, 7291 (2000).
b) S. Velusamy, J. S. K. Kumar, and T. Punniyamurthy, Tetrahedron Lett., 45, 203 (2004).
6) K. Ishihara, S. Ohara, and H. Yamamoto, Science, 290, 1140 (2000).
7) Note without reference.