Metal-Free Decarboxylative Alkoxylation of 2-Picolinic Acid and Its Derivatives with Cyclic Ethers: One Step Construction of C-O and C-Cl Bonds.
Xiaoqiang YuMin HeJianglin WuChuancheng ZhouXiujuan FengYoshinori YamamotoMing BaoPublished in: Organic letters (2018)
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 tBuOCl 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.
Keyphrases