Isoamyl Nitrite Activated Primary Sulfonamide to Sulfonyl Bromide and Sulfonyl Chloride
Sulfonyl bromide and sulfonyl chloride are important compounds commonly used as building blocks in organic synthesis.This paper presents the successful synthesis of sulfonyl bromide or sulfonyl chloride from primary sulfonamide using isoamyl nitrite(iAmONO)as an activator,dibromantine(DBDMH)as a bromine source,or trichloroisocyanuric acid(TCCA)as a chlorine source.The method offers several advantages such as wide range of raw materials,compatibility with various substrates,high yield,and mild reaction conditions.It is suitable for both gram-scale preparations and subsequent derivations,demonstrating practical value.Mechanistic studies suggest that N,N-dihalosulfonamide is a potential intermediate in this process and isoamyl nitrite plays a crucial role in the conversion process.
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