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Synthesis 2015; 47(20): 3186-3190
DOI: 10.1055/s-0034-1381024
DOI: 10.1055/s-0034-1381024
paper
tert-Butyl Hypochlorite Mediated Oxidative Chlorination of S-Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides
Weitere Informationen
Publikationsverlauf
Received: 03. Februar 2015
Accepted after revision: 13. Mai 2015
Publikationsdatum:
17. Juli 2015 (online)
Abstract
Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.
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