Buchumschlag

Electrochemical meta-C-H sulfonylation of pyridines with nucleophilic sulfinates

Considering the indispensable significance and utilities of meta-substituted pyridines in medicinal, chemical as well as materials science, a direct meta-selective C-H functionalization of pyridines is of paramount importance, but such reactions remain limited and highly challenging. In general, est...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Hauptverfasser: Qin, Shi (VerfasserIn) , Yang, Mingkai (VerfasserIn) , Xu, Mingyao (VerfasserIn) , Peng, Zhi-Huan (VerfasserIn) , Cai, Jiating (VerfasserIn) , Wang, Shengdong (VerfasserIn) , Gao, Hui (VerfasserIn) , Zhou, Zhi (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn) , Yi, Wei (VerfasserIn) , Zeng, Zhongyi (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2024
In: Nature Communications
Year: 2024, Jahrgang: 15, Pages: 1-8
ISSN:2041-1723
DOI:10.1038/s41467-024-50644-y
Online-Zugang:Verlag, kostenfrei, Volltext: https://doi.org/10.1038/s41467-024-50644-y
Verlag, kostenfrei, Volltext: https://www.nature.com/articles/s41467-024-50644-y
Volltext
Verfasserangaben:Shi Qin, Mingkai Yang, Mingyao Xu, Zhi-Huan Peng, Jiating Cai, Shengdong Wang, Hui Gao, Zhi Zhou, A. Stephen K. Hashmi, Wei Yi & Zhongyi Zeng
Beschreibung
Zusammenfassung:Considering the indispensable significance and utilities of meta-substituted pyridines in medicinal, chemical as well as materials science, a direct meta-selective C-H functionalization of pyridines is of paramount importance, but such reactions remain limited and highly challenging. In general, established methods for meta C-H functionalization of pyridines rely on the utilization of tailored electrophilic reagents to realize the intrinsic polarity match. Herein, we report a complementary electrochemical methodology; diverse nucleophilic sulfinates allow meta-sulfonylation of pyridines through a redox-neutral dearomatization-rearomatization strategy by a tandem dearomative cycloaddition/hydrogen-evolution electrooxidative C-H sulfonation of the resulting oxazino-pyridines/acid-promoted rearomatization sequence. Besides, several salient features, including exclusive regiocontrol, remarkable substrate/functional group compatibility, scale-up potential, and facile late-stage modification, have been demonstrated, which further contributes to the practicality and adaptability of this approach.
Beschreibung:Online veröffentlicht: 28. August 2024
Gesehen am 15.10.2025
Beschreibung:Online Resource
ISSN:2041-1723
DOI:10.1038/s41467-024-50644-y

Ähnliche Einträge