Tetrahedron p. 2183 - 2192 (1999)
Update date:2022-08-29
Topics:
Yoshida, Yoshihiro
Sakakura, Yoshiko
Aso, Naoya
Okada, Shin
Tanabe, Yoo
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. Et3N (0.1 equiv)/cat. Me3N · HCl (0.1 equiv) as the reagent, which will be suited for practical and large scale production for primary alcohols. On both methods A and B, a clear joint action of Et3N and Me3N · HCl catalysts was observed. 1H NMR measurements support the proposed mechanism of the catalytic cycle. Related methanesulfonylation using Et3N and cat. Me3N · HCl in toluene solvent also successfully proceeded, wherein the clear joint action was also observed.
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