10.1002/chem.201902811
Chemistry - A European Journal
COMMUNICATION
without olefin suggested the formation of
a palladacycle
Acknowledgements
(intermediate III, Scheme 8).[15]
This project has received funding from the INROAd initiative of
University of Pavia under the grant “UniCat" and SERB
(CRG/2018/003951), New Delhi, India.
Keywords: CH activation • meta-selectivity • fluorinated
compounds • palladium catalysis • iterative functionalization
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Scheme 7. Competition reaction between a non-deuterated and a deuterated
scaffold
On the basis of these results and previous literature reports, a
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(probably
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[6]
Scheme 8. Proposed catalytic cycle for the meta-perfluoroalkenylation
In conclusion, we reported the first palladium-catalyzed highly
selective meta-C(sp2)H perfluoroalkenylation of arenes. The
choice of a pyrimidine-based directing group is found to be crucial,
giving a high degree of compatibility with perfluoroolefins of
different nature. The synthetic versatility of the protocol was
demonstrated by a broad substrate scope including different
benzylsulfonyl, alkylaryl and phenylacetic acid scaffolds.
Ibuprofen CH perfluoroalkenylation, facile cleavage of the DG
and gram-scale reactions demonstrate the practical value of this
procedure.
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