Issue 3, 2022

Ring-opening fluorination of bicyclic azaarenes


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.

Graphical abstract: Ring-opening fluorination of bicyclic azaarenes

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Article information

Article type
Edge Article
12 Nov 2021
21 Dec 2021
First published
21 Dec 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 665-670

Ring-opening fluorination of bicyclic azaarenes

M. Komatsuda, A. Suto, H. Kondo, H. Takada, K. Kato, B. Saito and J. Yamaguchi, Chem. Sci., 2022, 13, 665 DOI: 10.1039/D1SC06273E

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