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 cl...

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Autores principales: Komatsuda, Masaaki, Suto, Ayane, Kondo, Hiroki, Takada, Hiroyuki, Kato, Kenta, Saito, Bunnai, Yamaguchi, Junichiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8768879/
https://www.ncbi.nlm.nih.gov/pubmed/35173930
http://dx.doi.org/10.1039/d1sc06273e
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author Komatsuda, Masaaki
Suto, Ayane
Kondo, Hiroki
Takada, Hiroyuki
Kato, Kenta
Saito, Bunnai
Yamaguchi, Junichiro
author_facet Komatsuda, Masaaki
Suto, Ayane
Kondo, Hiroki
Takada, Hiroyuki
Kato, Kenta
Saito, Bunnai
Yamaguchi, Junichiro
author_sort Komatsuda, Masaaki
collection PubMed
description 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.
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spelling pubmed-87688792022-02-15 Ring-opening fluorination of bicyclic azaarenes Komatsuda, Masaaki Suto, Ayane Kondo, Hiroki Takada, Hiroyuki Kato, Kenta Saito, Bunnai Yamaguchi, Junichiro Chem Sci Chemistry 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. The Royal Society of Chemistry 2021-12-21 /pmc/articles/PMC8768879/ /pubmed/35173930 http://dx.doi.org/10.1039/d1sc06273e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Komatsuda, Masaaki
Suto, Ayane
Kondo, Hiroki
Takada, Hiroyuki
Kato, Kenta
Saito, Bunnai
Yamaguchi, Junichiro
Ring-opening fluorination of bicyclic azaarenes
title Ring-opening fluorination of bicyclic azaarenes
title_full Ring-opening fluorination of bicyclic azaarenes
title_fullStr Ring-opening fluorination of bicyclic azaarenes
title_full_unstemmed Ring-opening fluorination of bicyclic azaarenes
title_short Ring-opening fluorination of bicyclic azaarenes
title_sort ring-opening fluorination of bicyclic azaarenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8768879/
https://www.ncbi.nlm.nih.gov/pubmed/35173930
http://dx.doi.org/10.1039/d1sc06273e
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