Visible-Light-Mediated Three-Component Decarboxylative Coupling Reactions for the Synthesis of 4‑Alkylpyridines

4-Alkylation of pyridines has been achieved by a photocatalyzed three-component reaction of an olefin, an aryloxyacetic acid, and cyanopyridine using Ir­[dF­(CF3)­ppy]2(dtbbpy)­PF6 as a photocatalyst. In this way, a new type of 4-alkylpyridines bearing aryl and aryloxy substituents on the phenyl was...

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Veröffentlicht in:Journal of organic chemistry 2024-12, Vol.89 (23), p.17382-17388
Hauptverfasser: Wang, Ai, Ma, Yijian, Jin, Jia-Hui, Wang, Le-Quan, Li, Dan-Dan, Xi, Zi-Wei, Shen, Chengshuo, Shen, Yong-Miao
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Sprache:eng
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Zusammenfassung:4-Alkylation of pyridines has been achieved by a photocatalyzed three-component reaction of an olefin, an aryloxyacetic acid, and cyanopyridine using Ir­[dF­(CF3)­ppy]2(dtbbpy)­PF6 as a photocatalyst. In this way, a new type of 4-alkylpyridines bearing aryl and aryloxy substituents on the phenyl was accessed with potential pharmaceutical value. In addition to mild reaction conditions, the method has several other advantages, including a multicomponent one-pot protocol, good functional group tolerance, and easy amplification of the reaction scale. The reaction mechanism has been clarified by control experiments and computation of the reaction energy profile.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02037