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Base‐Mediated O‐Arylation of Alcohols and Phenols by Triarylsulfonium Triflates
Author(s) -
Ming XiaoXia,
Tian ZeYu,
Zhang ChengPan
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900968
Subject(s) - chemistry , phenols , aryl , nucleophile , alkoxy group , base (topology) , phenol , primary (astronomy) , medicinal chemistry , organic chemistry , functional group , nucleophilic aromatic substitution , nucleophilic substitution , catalysis , alkyl , mathematical analysis , mathematics , polymer , physics , astronomy
A mild and efficient protocol for O‐arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition‐metal‐free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron‐donating or electron‐withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base‐mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C−S bonds of triarylsulfonium cations to furnish the target products.