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

Shi Qin, Mingkai Yang, Mingyao Xu, Zhi-Huan Peng, Jiating Cai, Shengdong Wang, Hui Gao, Zhi Zhou, A. Stephen K. Hashmi (), Wei Yi () and Zhongyi Zeng ()
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Shi Qin: Guangzhou Medical University
Mingkai Yang: Guangzhou Medical University
Mingyao Xu: Guangzhou Medical University
Zhi-Huan Peng: Guangzhou Medical University
Jiating Cai: Guangzhou Medical University
Shengdong Wang: Guangzhou Medical University
Hui Gao: Guangzhou Medical University
Zhi Zhou: Guangzhou Medical University
A. Stephen K. Hashmi: Heidelberg University
Wei Yi: Guangzhou Medical University
Zhongyi Zeng: Guangzhou Medical University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract 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.

Date: 2024
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DOI: 10.1038/s41467-024-50644-y

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