Palladium/Amine Dual-Catalyzed Tsuji–Trost Fluoroallylation of Aldehydes with <i>gem</i>-Difluorinated Cyclopropanes
Zhengquan Su, Binhong Tan, Zhaodong Li, Huicai Huang, Yue Zhang
Abstract
We herein disclose the Pd/amine dual-catalyzed ring-opening cross-coupling reaction between gem -difluorinated cyclopropanes ( gem -F 2 CPs) with aldehydes, which enables the diversity-oriented synthesis (DOS) of 2-fluoroallylic aldehydes bearing all-carbon quaternary centers with features of broad scope and excellent functional group tolerance. The synthetic value of this Tsuji–Trost system was further demonstrated by late-stage functionalization of natural product-derived gem -F 2 CPs and the diverse synthesis of various fluoroallylic aldehyde derivatives, including alcohol, alkyne, alkene, and amine.
Topics & Concepts
ChemistryPalladiumAmine gas treatingCatalysisRing (chemistry)Combinatorial chemistryDual (grammatical number)Medicinal chemistryOrganic chemistryArtLiteratureFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods