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.