Amination of Heteroaryl Chlorides: Palladium Catalysis or SNAr in Green Solvents?. Issue 8 (21st June 2013)

• Record Type: Journal Article
• Authors: Walsh, Katie; Sneddon, Helen F.; Moody, Christopher J.
• Is Part Of: ChemSusChem. Volume 6:Issue 8(2013:Aug.)
• Page Start: 1455
• Page End: 1460
• Publication Date: 2013-06-21
• Subjects: Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201300239
• Languages: English
• ISSNs: 1864-5631

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile S_NAr reaction and <italic>N</italic>‐arylation. The reaction is less satisfactory with pyridines unless an additional electron‐withdrawing group is present. The results showed that the transition‐metal‐free S_NAr reaction not only compares favourably to palladium‐catalysed coupling reactions but also operates under environmentally acceptable ("green") conditions in terms of the base and solvent.</p> </abstract>