10.1021/ol4030875.s001 Zhihui Liu Zhihui Liu Qiaoqiao Ma Qiaoqiao Ma Yuxiu Liu Yuxiu Liu Qingmin Wang Qingmin Wang 4‑(<i>N,N</i>-Dimethylamino)pyridine Hydrochloride as a Recyclable Catalyst for Acylation of Inert Alcohols: Substrate Scope and Reaction Mechanism American Chemical Society 2014 nucleophilic substrate Recyclable Catalyst acylation product Inert Alcohols acylating reagent catalyst DMAP salt Substrate Scope reaction mechanism 2014-01-03 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/4_i_N_N_i_Dimethylamino_pyridine_Hydrochloride_as_a_Recyclable_Catalyst_for_Acylation_of_Inert_Alcohols_Substrate_Scope_and_Reaction_Mechanism/2336467 4-(<i>N,N</i>-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 <i>N</i>-acyl-4-(<i>N′</i>,<i>N′</i>-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.