Department of Chemistry, Georgetown University , Washington, DC 20057, United States.
J Org Chem. 2017 Jan 20;82(2):1273-1278. doi: 10.1021/acs.joc.6b02704. Epub 2017 Jan 9.
An organocatalytic method that achieves insertion of isatins into aryl difluoronitromethyl ketones under mild conditions is described. The reaction occurs in the presence of 20 mol % of DBU and with 100% atom economy. A series of isatin derived difluoronitromethyl substituted tertiary alcohol benzoates and naphthoates were prepared in 81-99% yield. The general synthetic usefulness of these 3-hydroxyoxindole derivatives is demonstrated with the selective reduction to fluorooximes.
描述了一种在温和条件下实现吲哚酮插入芳基二氟硝酮的有机催化方法。该反应在 20mol%DBU 的存在下进行，原子经济性达到 100%。一系列吲哚酮衍生的二氟硝甲基取代的叔醇苯甲酸酯和萘酸酯以 81-99%的收率制备。这些 3-羟基色酮衍生物的一般合成用途通过选择性还原为氟肟得到证明。
