Metal-Free Decarboxylative Alkoxylation of 2‑Picolinic Acid and Its Derivatives with Cyclic Ethers: One Step Construction of C–O and C–Cl Bonds

A new strategy for the metal-free decarboxylative alkoxylation of 2-picolinic acid and its derivatives is described. The three-component reaction of 2-picolinic acid or its derivatives, cyclic ethers, and t BuOCl proceeded smoothly in the presence of a catalytic amount of p-chloranil to produce 2-al...

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Bibliographic Details
Published in:Organic letters 2018-11, Vol.20 (21), p.6780-6784
Main Authors: Yu, Xiaoqiang, He, Min, Wu, Jianglin, Zhou, Chuancheng, Feng, Xiujuan, Yamamoto, Yoshinori, Bao, Ming
Format: Article
Language:English
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Summary:A new strategy for the metal-free decarboxylative alkoxylation of 2-picolinic acid and its derivatives is described. The three-component reaction of 2-picolinic acid or its derivatives, cyclic ethers, and t BuOCl proceeded smoothly in the presence of a catalytic amount of p-chloranil to produce 2-alkoxylated pyridines with an ω-chlorine atom in satisfactory to excellent yields. New C–O and C–Cl bonds were generated in one step. The ω-C–Cl bond can be easily transformed to a C–C or C–heteroatom bond, increasing the use of 2-alkoxylated pyridine products in organic synthesis. The electronic property of the substituent linked on the pyridine ring did not influence the reactivity of the 2-picolinic acid substrates.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02896