An efficient and straightforward approach for accessing sulfonamide/ N -sulfonyl succinic esters via potassium fluoride-promoted C–N cleavage of N -sulfonyl succinimide

We report herein a two-step one-pot strategy for the synthesis of sulfonamides/ N -sulfonyl succinic esters from N -sulfonyl succinimide by using potassium fluoride as a promoter. This approach involves the in situ generation of the N -sulfonyl succinimide additional product by KF, further reacted w...

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Published inNew journal of chemistry Vol. 48; no. 14; pp. 6378 - 6385
Main Authors Lu, Zujia, Yang, Guangzao, Luo, Huaxin, Gao, Minjie, Irfan, Majeed, Wang, Fei, Zeng, Zhuo
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 02.04.2024
Subjects
Alcohols
Carbonyl groups
Carbonyls
Cleavage
Esters
Potassium fluoride
Sulfonamides
Synthesis
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Summary:We report herein a two-step one-pot strategy for the synthesis of sulfonamides/ N -sulfonyl succinic esters from N -sulfonyl succinimide by using potassium fluoride as a promoter. This approach involves the in situ generation of the N -sulfonyl succinimide additional product by KF, further reacted with alcohols to yield N -sulfonyl succinic esters by C–N cleavage, whereas sulfonamides are obtained via hydrolysis. Moreover, the S–N bond in sulfonamide displays inert behavior, which results in KF activating the carbonyl group of succinimide. Notably, this new approach employs N -sulfonyl succinimide to give sulfonamides/ N -sulfonyl succinic esters in good to excellent yields. This protocol can be efficiently utilized in the synthesis of broad sulfonamides/ N -sulfonyl succinic esters under a simple potassium fluoride promoter and metal-free conditions.
ISSN:1144-0546
1369-9261
DOI:10.1039/D4NJ00330F