Ring-opening Fluorination of Bicyclic Azaarenes

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Feb 17

PMID 35173930

Authors

Masaaki Komatsuda

Ayane Suto

Hiroki Kondo Jr

Hiroyuki Takada

Kenta Kato

Bunnai Saito

Junichiro Yamaguchi

Affiliations

Soon will be listed here.

Abstract

We have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolo[1,5-]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.

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Ring-opening fluorination of bicyclic azaarenes.

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