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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...

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Auteurs principaux: Qin, Shi (Auteur) , Yang, Mingkai (Auteur) , Xu, Mingyao (Auteur) , Peng, Zhi-Huan (Auteur) , Cai, Jiating (Auteur) , Wang, Shengdong (Auteur) , Gao, Hui (Auteur) , Zhou, Zhi (Auteur) , Hashmi, A. Stephen K. (Auteur) , Yi, Wei (Auteur) , Zeng, Zhongyi (Auteur)
Format: Article (Journal)
Langue:anglais
Publié: 2024
In: Nature Communications
Year: 2024, Volume: 15, Pages: 1-8
ISSN:2041-1723
DOI:10.1038/s41467-024-50644-y
Accès en ligne:Verlag, kostenfrei, Volltext: https://doi.org/10.1038/s41467-024-50644-y
Verlag, kostenfrei, Volltext: https://www.nature.com/articles/s41467-024-50644-y
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Notes sur l'auteur: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
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Résumé: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.
Description:Online veröffentlicht: 28. August 2024
Gesehen am 15.10.2025
Description matérielle:Online Resource
ISSN:2041-1723
DOI:10.1038/s41467-024-50644-y

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