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Direct meta ‐C−H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine‐Based Template
Author(s) -
Brochetta Massimo,
Borsari Tania,
Bag Sukdev,
Jana Sadhan,
Maiti Siddhartha,
Porta Alessio,
Werz Daniel B.,
Zai Giuseppe,
Maiti Debabrata
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902811
Subject(s) - pyrimidine , combinatorial chemistry , phenylacetic acid , chemistry , substrate (aquarium) , generality , stereochemistry , organic chemistry , biology , psychology , ecology , psychotherapist
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.