Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides
Dayong Sang, Bingqian Dong, Yunfeng Liu, Juan Tian
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.
Topics & Concepts
ChemistryHalideAlkylationAcetonitrileAlkylCleavage (geology)Medicinal chemistryNitrileBond cleavageOrganic chemistryCatalysisEngineeringFracture (geology)Geotechnical engineeringAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisChemical Synthesis and Reactions