Direct meta‐C−H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine‐Based Template

The development of efficient and mild methods for the synthesis of organofluorine compounds is of foremost interest in various fields of chemistry. A direct pyrimidine‐based selective meta‐C−H perfluoroalkenylation of arenes involving several commercially available perfluoroolefins is described. The...

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Published in:Chemistry : a European journal 2019-08, Vol.25 (44), p.10323-10327
Main Authors: Brochetta, Massimo, Borsari, Tania, Bag, Sukdev, Jana, Sadhan, Maiti, Siddhartha, Porta, Alessio, Werz, Daniel B., Zanoni, Giuseppe, Maiti, Debabrata
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Language:English
Subjects:
Aromatic compounds
Chemistry
C−H activation
fluorinated compounds
Ibuprofen
iterative functionalization
meta-selectivity
Organic chemistry
Organofluorine compounds
palladium catalysis
Perfluoro compounds
Phenylacetic acid
Substrates
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cited_by cdi_FETCH-LOGICAL-c4761-692b45315b988f96d4b282da8f9bd0e2e5a1a336b8b8795864a6af75ba95c8313
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container_end_page 10327
container_issue 44
container_start_page 10323
container_title Chemistry : a European journal
container_volume 25
creator Brochetta, Massimo
Borsari, Tania
Bag, Sukdev
Jana, Sadhan
Maiti, Siddhartha
Porta, Alessio
Werz, Daniel B.
Zanoni, Giuseppe
Maiti, Debabrata
description The development of efficient and mild methods for the synthesis of organofluorine compounds is of foremost interest in various fields of chemistry. A direct pyrimidine‐based selective meta‐C−H perfluoroalkenylation of arenes involving several commercially available perfluoroolefins is described. The synthetic versatility of the protocol is demonstrated by an extensive substrate scope including different benzylsulfonyl, alkylarene and phenylacetic acid scaffolds. The generality of this methodology including the meta‐C−H perfluoroalkenylation of Ibuprofen, the facile cleavage of the directing group and gram‐scale reactions are presented. Right to the point: A palladium(II)‐catalyzed meta‐selective C−H perfluoroalkenylation of arenes utilizing readily available fluorinated olefins is described. The practicability of this transformation has been demonstrated by selective perfluoroolefination of the pharmaceutical Ibuprofen.
doi_str_mv 10.1002/chem.201902811
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subjects Aromatic compounds
Chemistry
C−H activation
fluorinated compounds
Ibuprofen
iterative functionalization
meta-selectivity
Organic chemistry
Organofluorine compounds
palladium catalysis
Perfluoro compounds
Phenylacetic acid
Substrates
title Direct meta‐C−H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine‐Based Template
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