Kawanishi Ryouta, Phongphane Lacksany, Iwasa Seiji, Shibatomi Kazutaka
Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi, 441-8580, Japan.
Chemistry. 2019 Jun 4;25(31):7453-7456. doi: 10.1002/chem.201900565. Epub 2019 Apr 26.
Syntheses of substituted pyridines and fluorinated compounds, which are often pharmaceutical targets, are important objectives in organic chemistry. Herein, we found that decarboxylative fluorination of lithium 2-pyridylacetates occur under catalyst-free conditions. The phenomenon can be applied to one-pot transformation of substituted methyl 2-pyridylacetate to 2-(fluoroalkyl)pyridine by decarboxylative fluorination of the intermediate lithium 2-pyridylacetate. This method was also applied to the syntheses of 2-(difluoroalkyl)pyridines.
取代吡啶和含氟化合物的合成是有机化学中的重要目标,它们常常是药物靶点。在此,我们发现2-吡啶基乙酸锂的脱羧氟化反应在无催化剂条件下即可发生。该现象可应用于将取代的2-吡啶基乙酸甲酯通过中间体2-吡啶基乙酸锂的脱羧氟化一锅法转化为2-(氟烷基)吡啶。此方法还可应用于2-(二氟烷基)吡啶的合成。