Synthesis of 2-Arylbenzoxazoles via the Palladium-Catalyzed Carbonylation and Condensation of Aromatic Halides and o-Aminophenols

Article abstract of DOI:10.1021/jo00036a025

A new synthetic method is reported in which 2-arylbenzoxazoles can be prepared by palladium-catalyzed condensation of aryl halides with o-aminophenols followed by dehydrative cyclization.This method is tolerant of a wide variety of functional groups on either aromatic ring and gives good to excellent yields of products.An aliphatic vicinal amino alcohol gave a bis-acylated product as well as a chlorine-containing product with only a small amount of the desired 2-aryloxazole being formed.Methyl iodide and benzyl bromide gave only alkylated products.