Catalytic Alkynylation of Heterocyclic Ketones in Zn(OTf)₂/TBAF·۳H₂O System

Catalytic alkynylation of heterocyclic ketones was investigated using Zn(OTf)₂/TBAF·۳H₂O system under mild reaction conditions. A series of heterocyclic ketones containing furan-۲-yl, thiophen-۲-yl, pyridin-۴-yl, and ۵-chlorothiophen-۲-yl substituents were successfully converted into the corresponding acetylenic alcohols in moderate to high yields. The effects of catalyst loading, reaction temperature, and reaction time on the efficiency of the alkynylation process were systematically studied, and the optimal conditions were established. The highest product yields were obtained at −۱۰ °C using ۰.۰۵ mol of the catalytic system and a reaction time of ۱۲۰ min. The synthesized compounds were characterized by ¹H- and ¹³C-NMR spectroscopy. Additionally, quantum-chemical calculations were performed to evaluate the electronic and structural properties of the obtained acetylenic alcohols. The results demonstrate that the Zn(OTf)₂/TBAF·۳H₂O catalytic system provided an efficient and convenient approach for the synthesis of heterocyclic acetylenic alcohols under relatively mild conditions. Furthermore, the obtained results expand the available data on Zn-based catalytic alkynylation systems and may contribute to the further development of heterocyclic acetylenic compounds for synthetic and structural chemistry applications.

کلیدواژه ها:

Acetylenic alcohols ، Alkynylation ، Heterocyclic ketones ، Catalytic system