Issue 3, 2022

Ring-opening fluorination of bicyclic azaarenes

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.

Graphical abstract: Ring-opening fluorination of bicyclic azaarenes

Supplementary files

Article information

Article type
Edge Article
Submitted
12 Nov 2021
Accepted
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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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