Selective C–F Bond Etherification of Trifluoromethylalkenes with Phenols

Selective functionalization of a single sp3 C–F bond of the CF3 group represents an appealing way to generate the pharmaceutically privileged difluoromethylene moiety. Herein, a novel protocol for the C–F bond etherification of trifluoromethylalkenes and phenols is reported. A variety of alkenyl dif...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2022-08, Vol.87 (16), p.10908-10916
Main Authors: Tian, Qingqiang, Pei, Boqun, Wang, Chuxia, Zhang, Chiying, Li, Yahui
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Selective functionalization of a single sp3 C–F bond of the CF3 group represents an appealing way to generate the pharmaceutically privileged difluoromethylene moiety. Herein, a novel protocol for the C–F bond etherification of trifluoromethylalkenes and phenols is reported. A variety of alkenyl difluoroaryloxy ethers are obtained with good chemoselectivity and functional group tolerance. DFT calculation results and control experiments suggest that metal ion Cs+ might be involved in this defluorooxylation. Furthermore, the desired product exhibits a good insecticidal activity.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01197