Tetrahedron

One-pot synthesis of sulfonamides from methyl sulfinates using ultrasound

JLG Ruano, A Parra, L Marzo, F Yuste, VM Mastranzo

Index: Garcia Ruano, Jose L.; Parra, Alejandro; Marzo, Leyre; Yuste, Francisco; Mastranzo, Virginia M. Tetrahedron, 2011 , vol. 67, # 16 p. 2905 - 2910

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Citation Number: 20

Abstract

Room temperature ultrasonic irradiation of neat mixtures of methyl sulfinates and primary or secondary amines (1.5 equiv) produced sulfinamides, which on m-CPBA oxidation (in dichloromethane) were converted into the corresponding sulfonamides. The two steps can be accomplished in one pot, in good overall yields, when using secondary amines, but primary amines give better sulfonamide yields when the peracid oxidation is effected on ...