4.6 Article

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

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 44, Pages 10323-10327

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201902811

Keywords

C-H activation; fluorinated compounds; iterative functionalization; meta-selectivity; palladium catalysis

Funding

  1. INROAd initiative of University of Pavia under the grant UniCat
  2. SERB, New Delhi, India [CRG/2018/003951]

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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.

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