Photoinduced -Aminoalkylation of Sulfonylarenes with Alkylamines

alpha-Aminoalkylation of sulfonylarenes with alkylamines was found to be induced by photoirradiation. Here various types of alkylamines, such as trialkylamines, dialkylamines, N,N-dialkylanilines and N-alkylanilines as well as sulfonylarenes containing an azole, azine, heterole or benzene ring are available. The reaction proceeds through a homolytic aromatic substitution (HAS) process consisting of addition of an alpha-aminoalkyl radical to a sulfonylarene and elimination of the sulfonyl radical to give the alpha-arylalkylamine, where photoirradiation is considered to induce homolysis of sulfonylarenes leading to the generation of alpha-aminoalkyl radicals that make a radical chain operative.