Affiliation:
1. Department of Applied Chemistry for Environment School of Biological and Environmental Sciences Kwansei Gakuin University 1 Gakuen Uegahara Sanda Hyogo 669-1330 Japan
2. Department of Chemistry Graduate School of Advanced Science and Engineering Hiroshima University Higashi-Hiroshima Hiroshima 739-8526 Japan
Abstract
Abstractα‐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 α‐aminoalkyl radical to a sulfonylarene and elimination of the sulfonyl radical to give the α‐arylalkylamine, where photoirradiation is considered to induce homolysis of sulfonylarenes leading to the generation of α‐aminoalkyl radicals that make a radical chain operative.
Funder
Japan Science and Technology Corporation
Japan Society for the Promotion of Science
Subject
General Chemistry,Catalysis,Organic Chemistry
Reference48 articles.
1. For examples see:
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3. A Structural Analysis of the FDA Green Book-Approved Veterinary Drugs and Roles in Human Medicine
4. Besides α-aminoalkyl radicals α-aminoalkyl anions and cations are used as intermediates for α-arylation of alkylamines. Most of the methods using α-aminoalkyl anions or cations require multiple-step procedure and offer a limited scope of substrates. The method using the anions is typically achieved by a sequence of acylation of alkylamines deprotonation by butyllithium transmetalation with zinc chloride the Negishi coupling with aryl halides and deacylation. For a review see:
5. Direct α-Functionalization of Saturated Cyclic Amines