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

Dağalan Z., Çelikoğlu M. H., Nişancı B., Çelik S., Koçak R.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol.20, pp.1462-1467, 2024 (SCI-Expanded, Scopus) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 20
  • Publication Date: 2024
  • Doi Number: 10.3762/bjoc.20.129
  • Journal Name: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, Chemical Abstracts Core, Directory of Open Access Journals
  • Page Numbers: pp.1462-1467
  • Ataturk University Affiliated: Yes

Abstract

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.