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...

Full description

Saved in:
Bibliographic Details
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
Format: Article
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
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: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201902811