Selectfluor and alcohol-mediated synthesis of bicyclic oxyfluorination compounds by Wagner-Meerwein rearrangement

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Daǧalan Z., ÇELİKOĞLU M. H., ÇELİK S., Koçak R., NİŞANCI B.

Beilstein Journal of Organic Chemistry, cilt.20, ss.1462-1467, 2024 (SCI-Expanded, Scopus) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 20
  • Basım Tarihi: 2024
  • Doi Numarası: 10.3762/bjoc.20.129
  • Dergi Adı: Beilstein Journal of Organic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, Chemical Abstracts Core, Directory of Open Access Journals
  • Sayfa Sayıları: ss.1462-1467
  • Anahtar Kelimeler: alkoxyfluorine compounds, bicyclic alkene, oxyfluorination, selectfluor, Wagner-Meerwein rearrangement
  • Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
  • Trakya Üniversitesi Adresli: Evet

Özet

Herein, we report the first environmentally friendly systematic fluoroalkoxylation reactions in bicyclic systems. New oxyfluorination products were obtained with excellent yields (up to 98%) via Wagner-Meerwein rearrangement using benzonorbornadiene and the chiral natural compound (+)-camphene as bicyclic alkenes, selectfluor as an electrophilic fluorine source, and water and various alcohols as nucleophile sources. The structure of bicyclic oxy- and alkoxyfluorine compounds was determined by NMR and QTOFMS analyses.