학술논문

Sequential Xanthalation and O‑Trifluoromethylation of Phenols: A Procedure for the Synthesis of Aryl Trifluoromethyl Ethers
Document Type
article
Source
The Journal of Organic Chemistry. 84(24)
Subject
Organic Chemistry
Chemical Sciences
Ethers
Hydrocarbons
Fluorinated
Molecular Structure
Phenols
Xanthines
Medicinal and Biomolecular Chemistry
Medicinal and biomolecular chemistry
Organic chemistry
Language
Abstract
Molecules containing trifluoromethoxyaryl groups are of interest in pharmaceutical, agrochemical, and materials science research, due to their unique physical and electronic properties. Many of the known methods to synthesize aryl trifluoromethyl ethers require harsh reagents and highly controlled reaction conditions and rarely occur when heteroaromatic units are present. The two-step O-trifluoromethylation of phenols via aryl xanthates is one such method that suffers from these drawbacks. Herein, we report a method for the synthesis of aryl trifluoromethyl ethers from phenols by the facile conversion of the phenol to the corresponding aryl and heteroaryl xanthates with newly synthesized imidazolium methylthiocarbonothioyl salts and conversion of these xanthates to the trifluoromethyl ethers under mild reaction conditions.