Regioselective and site-divergent synthesis of tetrahydropyridines by controlled reductive-oxidative dearomative hydroarylation of pyridinium salts.

Xing-Fu Wei, Shan Wang, Yu-Long Li, Qiong Yu, Wei Shu

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Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

Xing-Fu WeiShenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute, and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, P. R. China.

Shan WangShenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute, and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, P. R. China.

Yu-Long LiCollege of Chemistry and Environmental Engineering and Innovation Center for Chenguang High Performance Fluorine Material, Sichuan University of Science and Engineering, Zigong, Sichuan, P. R. China. yu_longli@suse.edu.cn.ORCID http://orcid.org/0000-0002-5579-3269

Qiong YuShenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute, and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, P. R. China. yuq3@mail.sustech.edu.cn.ORCID http://orcid.org/0009-0008-9529-4799

Wei ShuShenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute, and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, P. R. China. shuw@sustech.edu.cn.ORCID http://orcid.org/0000-0003-0890-2634

Funding

Basic Research Programs of Sichuan Province 2025ZNSFSC0128Guangdong Science and Technology Department (Science and Technology Department, Guangdong Province) 2019QN01Y261, 2020B121201002National Natural Science Foundation of China (National Science Foundation of China) 22171127, 22371115, 22373056Shenzhen Science and Technology Innovation Commission JCYJ20230807093522044, JCYJ20240813094226034

6 · The paper itself

Abstract

Tetrahydropyridine skeletons serve as ubiquitous structural motifs which are predominant in natural products, bioactive and drug molecules. Thus, the development of efficient and general synthetic methods for the synthesis of tetrahydropyridine frameworks with different substitutions has attracted great attention from the community. Moreover, the control of regioselectivity and site-divergency remains an unmet challenge. Herein, we report a regioselective and site-divergent reductive hydroarylation of pyridinium salts with aryl nucleophiles, enabling direct access to diverse tetrahydropyridine derivatives with aryl substitution at different positions under mild conditions. Mechanistic studies support that the reaction underwent a CoH-mediated double-reduction process of pyridinium salts.

Identifiers

PMID41290676

DOI10.1038/s41467-025-65735-7

PMCPMC12663418

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.