4-(N,N-Dimethylamino)pyridine Hydrochloride as a Recyclable Catalyst for Acylation of Inert Alcohols: Substrate Scope and Reaction Mechanism

4-(N,N-Dimethylamino)pyridine hydrochloride (DMAP center dot HCl), a DMAP salt with the simplest structure, was used as a recyclable catalyst for the acylation of inert alcohols and phenols under base-free conditions. The reaction mechanism was investigated in detail for the first time; DMAP center dot HCl and the acylating reagent directly formed N-acyl-4-(N',N'-dimethylamino)pyridine chloride, which was attacked by the nucleophilic substrate to form a transient intermediate that released the acylation product and regenerated the DMAP center dot HCl catalyst.