Ring-opening fluorination of bicyclic azaarenes

Masaaki Komatsuda, Ayane Suto, Hiroki Kondo, Hiroyuki Takada, Kenta Kato, Bunnai Saito, Junichiro Yamaguchi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

We have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolo[1,5-a]pyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall transformation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon-fluorine bonds. The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups. Additionally, mechanistic studies and enantioselective fluorination have been examined.

Original languageEnglish
Pages (from-to)665-670
Number of pages6
JournalChemical Science
Volume13
Issue number3
DOIs
Publication statusPublished - 2022 Jan 21

ASJC Scopus subject areas

  • Chemistry(all)

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