Iodine(III)-Mediated Fluorination/Semipinacol Rearrangement Cascade of 2-Alkylidenecyclobutanol Derivatives: Access to β-Monofluorinated Cyclopropanecarbaldehydes
Si-Xin Feng, Shuang Yang, Fang‐Hai Tu, Peng-Peng Lin, Long-Ling Huang, Honggen Wang, Zhi‐Shu Huang, Qingjiang Li
Abstract
A hypervalent iodine(III)-mediated ring-contractive fluorination reaction of 2-alkylidenecyclobutanol derivatives is presented. The protocol allows the facile synthesis of β-monofluorinated cyclopropanecarbaldehydes via a fluorination/semipinacol rearrangement cascade using nucleophilic Py·HF as the fluorine source. For challenging electron-rich arene substrates, the installation of a protecting group on the free alcohol is pivotal for maintaining the reaction efficiency. The synthetic utility was demonstrated by the scalability of this reaction and further transformations of the products.
Topics & Concepts
Hypervalent moleculeChemistryIodineNucleophileCombinatorial chemistryFluorineRing (chemistry)AlcoholMedicinal chemistryOrganic chemistryCatalysisFluorine in Organic ChemistryCarbohydrate Chemistry and SynthesisCyclopropane Reaction Mechanisms