The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl and AlI display complementary reactivities toward -alkyl and -acyl moieties. -Alkylacylsulfonamides, secondary -(-butyl)sulfonamides, and tertiary -(-butyl)amides undergo N-dealkylation upon treatments with AlI generated in situ from aluminum and iodine in acetonitrile. In contrast, AlCl preferentially cleaves -acyl groups of tertiary and secondary sulfonamides.
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