TMSCF3 as a Convenient Source of CF2=CF2 for Pentafluoroethylation, (Aryloxy)tetrafluoroethylation, and Tetrafluoroethylation

A new method for the on‐site preparation of tetrafluoroethylene (TFE) and a procedure for its efficient use in pentafluoroethylation by fluoride addition were developed by using a simple two‐chamber system. The on‐site preparation of TFE was accomplished by dimerization of difluorocarbene derived fr...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-08, Vol.56 (33), p.9971-9975
Main Authors: Li, Lingchun, Ni, Chuanfa, Xie, Qiqiang, Hu, Mingyou, Wang, Fei, Hu, Jinbo
Format: Article
Language:English
Subjects:
copper
difluorocarbene
Dimerization
Fluorides
pentafluoroethylation
tetrafluoroethylation
Tetrafluoroethylene
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new method for the on‐site preparation of tetrafluoroethylene (TFE) and a procedure for its efficient use in pentafluoroethylation by fluoride addition were developed by using a simple two‐chamber system. The on‐site preparation of TFE was accomplished by dimerization of difluorocarbene derived from (trifluoromethyl)trimethylsilane (TMSCF3) under mild conditions. Other fluoroalkylation reactions, such as (aryloxy)tetrafluoroethylation and tetrafluoroethylation processes, were also achieved using a similar approach. This work not only demonstrates a convenient and safe approach for the generation and use of TFE in academic laboratories, but also provides a new strategy for pentafluoroethylation. In your own lab: The on‐site generation of CF2=CF2 from TMSCF3 under mild conditions is possible with a two‐chamber system and can be used for per‐ or polyfluoroalkylation. This study describes a convenient and safe approach for the use of CF2=CF2 in standard laboratories, and provides a new method for pentafluoroethylation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201705734