Tetrahedron

Practical and efficient methods for sulfonylation of alcohols using Ts (Ms) Cl/Et 3 N and catalytic Me 3 H· HCl as combined base: Promising alternative to traditional …

Y Yoshida, Y Sakakura, N Aso, S Okada, Y Tanabe

Index: Yoshida, Yoshihiro; Sakakura, Yoshiko; Aso, Naoya; Okada, Shin; Tanabe, Yoo Tetrahedron, 1999 , vol. 55, # 8 p. 2183 - 2192

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Citation Number: 163

Abstract

Several alcohols were smoothly and practically tosylated by two methods A and B. Method A uses the TsCl/Et3N (1.5–2.5 equiv)/cat. Me3N· HCl (0.1–1.0 equiv) reagent. Compared with the traditional Py-solvent method, the method A has merits of its much higher reaction rate, operational simplicity, economy in the use of the amine, and circumvention of the undesirable side reaction from R-OTs to R-Cl. Method B uses TsCl/KOH [or Ca (OH) 2]/cat. ...