2014
DOI: 10.1021/co400164z
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Sulfonyl Fluorides as Alternative to Sulfonyl Chlorides in Parallel Synthesis of Aliphatic Sulfonamides

Abstract: Two types of aliphatic sulfonyl halides (Cl versus F) were compared in parallel synthesis of sulfonamides derived from aliphatic amines. Aliphatic sulfonyl fluorides showed good results with amines bearing an additional functionality, while the corresponding chlorides failed. Both sulfonyl halides were effective in the reactions with amines having an easily accessible amino group. Aliphatic sulfonyl chlorides reacted efficiently with amines bearing sterically hindered amino group while the corresponding fluori… Show more

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Cited by 72 publications
(69 citation statements)
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“…[31] Owing to their high reactivity,a liphatic sulfonyl chlorides had low selectivity in the reaction with polyfunctionala mines. [31] Owing to their high reactivity,a liphatic sulfonyl chlorides had low selectivity in the reaction with polyfunctionala mines.…”
Section: Resultsmentioning
confidence: 99%
“…[31] Owing to their high reactivity,a liphatic sulfonyl chlorides had low selectivity in the reaction with polyfunctionala mines. [31] Owing to their high reactivity,a liphatic sulfonyl chlorides had low selectivity in the reaction with polyfunctionala mines.…”
Section: Resultsmentioning
confidence: 99%
“…Next, we expanded our collection of building blocks into sulfonyl chlorides . Reaction of mesylates 23 d – 26 d with sodium thioacetate in DMF at room temperature gave thioacetates 23 i – 26 i .…”
Section: Resultsmentioning
confidence: 99%
“…Sulfonyl fluorides have been employed as starting material for the synthesis of sulfonamides long before the concept of SuFEx chemistry, and a number of reports have demonstrated the advantages of sulfonyl fluorides over the more common starting‐material, sulfonyl chlorides, especially for aliphatic and heteroaromatic derivatives . In 2018, Ball and co‐workers reported a new method for the coupling of aryl‐ and alkylsulfonyl fluorides and amines that proceeds under calcium triflimide activation (Scheme ) .…”
Section: Addendummentioning
confidence: 99%