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Updated: Oct 3, 2025

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Published on: April 2, 2018
Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides
Dayong Sang1, Bingqian Dong1,2, Yunfeng Liu1
1College of Chemical Engineering and Pharmacy, Jingchu University of Technology, Jingmen, Hubei 448000, P. R. China.
Abstract:
The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3 and AlI3 display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, secondary N-(tert-butyl)sulfonamides, and tertiary N-(tert-butyl)amides undergo N-dealkylation upon treatments with AlI3 generated in situ from aluminum and iodine in acetonitrile. In contrast, AlCl3 preferentially cleaves N-acyl groups of tertiary and secondary sulfonamides.
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