醇和酚的银介导氧化五氟乙基化合成五氟乙基醚。

Synthesis of Pentafluoroethyl Ethers by Silver-Mediated Oxidative Pentafluoroethylation of Alcohols and Phenols.

机构信息

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.

College of Chemistry, Chemical Engineering, and Biotechnology, Donghua University , 2999 North Renmin Lu, Shanghai 201620, China.

出版信息

J Org Chem. 2017 Apr 7;82(7):3702-3709. doi: 10.1021/acs.joc.7b00190. Epub 2017 Mar 20.

DOI:10.1021/acs.joc.7b00190

PMID:28291342

Abstract

A silver triflate (AgOTf)-mediated oxidative pentafluoroethylation of alcohols and phenols with nucleophilic (pentafluoroethyl)trimethylsilane (TMSCFCF) using selectfluor as oxidant under mild reaction conditions was developed. This oxidative coupling protocol utilizes broadly available substrates and easily handled reagents to afford various pentafluoroethyl ethers in moderate to excellent yields. Furthermore, this method was extended to the oxidative heptafluoropropylation and ethoxycarbonyldifluoromethylation of alcohols and phenols for preparation of the corresponding fluoroalkyl ethers.

摘要

发展了一种在温和条件下，使用银三氟甲磺酸酯（AgOTf）介导的亲核（五氟乙基）三甲基硅烷（TMSCFCF）对醇和酚进行五氟乙基化的方法，该方法使用 Selectfluor 作为氧化剂。该氧化偶联反应使用了广泛可用的底物和易于处理的试剂，以中等至优异的产率得到了各种五氟乙基醚。此外，该方法还扩展到了醇和酚的七氟丙基化和乙氧羰二氟甲基化的氧化反应，以制备相应的氟烷基醚。