Palladium-Catalyzed Allylation of P(O)H Compounds: Access to 2-Fluoroallylic Phosphorus Compounds
Jie Sun, Hao Ye, Fei Sun, Yi-Yun Pan, Xi-Wei Zhu, Xin‐Xing Wu
Abstract
An efficient palladium-catalyzed 2-fluoroallylation of P(O)H compounds with gem -difluorocyclopropanes is presented. The reaction provides a variety of 2-fluoroallylic phosphorus compounds in good yields with high Z selectivity through the sequential C–C bond activation, C–F bond cleavage, and C–P coupling process. Various H-phosphonates, H-phosphinates, and secondary phosphine oxides are all tolerated. In addition, the gram-scale synthesis and the late-stage modification of complex bioactive molecules show practical utilities of the transformation.
Topics & Concepts
ChemistryPalladiumCatalysisPhosphorusMedicinal chemistryOrganic chemistryCombinatorial chemistryAsymmetric Hydrogenation and CatalysisOrganophosphorus compounds synthesisCatalytic Cross-Coupling Reactions