Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent

DN D'Aleo, SR Allard, CC Foglia…

Index: D'Aleo, Danielle N.; Allard, Sheena R.; Foglia, Cassandra C.; Parent, Shawna L.M.; Rohr, David J.; Gottardo, Christine; MacKinnon, Craig D. Canadian Journal of Chemistry, 2013 , vol. 91, # 8 p. 679 - 683

Full Text: HTML

Citation Number: 3

Abstract

The green generation of X+ (X= Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quantitative for positions α to the sulfur; pyrroles also give quantitative reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as ...