One-pot synthesis of sulfonamides from methyl sulfinates using ultrasound

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 ov...

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Bibliographic Details
Published in:Tetrahedron 2011-04, Vol.67 (16), p.2905-2910
Main Authors: García Ruano, José L., Parra, Alejandro, Marzo, Leyre, Yuste, Francisco, Mastranzo, Virginia M.
Format: Article
Language:English
Subjects:
Amines
Chemistry
Chlorides
Dichloromethane
Exact sciences and technology
General and physical chemistry
Kinetics and mechanisms
Methyl sulfinates
Organic chemistry
Oxidation
Peracids
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Reactivity and mechanisms
Sulfinamides
Sulfonamides
Synthesis (chemistry)
Tetrahedrons
Ultrasonic chemistry
Ultrasound
Utrasound
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Summary: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 the purified sulfinamide. This constitutes a mild, efficient, and potentially scalable route to sulfonamides, which obviates the use of water sensitive, often lachrymatory sulfonyl chlorides and large reagent excesses. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.02.060