Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 33, Pages 9971-9975Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705734
Keywords
copper; difluorocarbene; pentafluoroethylation; tetrafluoroethylation; tetrafluoroethylene
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Funding
- National Basic Research Program of China [2015CB931900]
- National Natural Science Foundation of China [21632009, 21472221, 21421002, 21372246]
- Chinese Academy of Sciences [KGZD-EW-T08]
- CAS [QYZDJ-SSW-SLH049]
- Shanghai Academic Research Leader Program [15XD1504400]
- Shanghai Rising-Star Program [16QA1404600]
- Youth Innovation Promotion Association CAS [2014231]
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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.
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