ol4030875_si_001.pdf (4.67 MB)
4‑(N,N-Dimethylamino)pyridine Hydrochloride as a Recyclable Catalyst for Acylation of Inert Alcohols: Substrate Scope and Reaction Mechanism
journal contribution
posted on 2014-01-03, 00:00 authored by Zhihui Liu, Qiaoqiao Ma, Yuxiu Liu, Qingmin Wang4-(N,N-Dimethylamino)pyridine hydrochloride (DMAP·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·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·HCl catalyst.