One-pot synthesis of sulfonamides from methyl sulfinates using ultrasound |
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Authors: | José L. Garcí a Ruano,Alejandro ParraLeyre Marzo,Francisco YusteVirginia M. Mastranzo |
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Affiliation: | a Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain b Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Cd. Universitaria, Coyoacán 04510, México D.F., Mexico |
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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 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. |
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Keywords: | Sulfonamides Utrasound Methyl sulfinates Sulfinamides |
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