Convergent Synthesis of Fluoroalkenes Using a Dual-Reactive Unit
Motoyuki Isoda, Yuta Uetake, Tadashi Takimoto, Junpei Tsuda, Takamitsu Hosoya, Takashi Niwa
Abstract
Fluoroalkenes have shown importance as a metabolically stable isostere of amide compounds. To expedite the synthesis of diverse fluoroalkenes, we have developed a dual-reactive C2-unit, (Z)-1-boryl-1-fluoro-2-tosyloxyethene, containing nucleophilic and electrophilic moieties. Consecutive palladium-catalyzed cross-coupling reactions of this unit with aryl bromides and aryl boronic acids allow for the convergent synthesis of diverse trans-1,2-diaryl-substituted fluoroethenes in a chemoselective and stereoretentive manner.
Topics & Concepts
ChemistryIsostereElectrophileConvergent synthesisNucleophileArylAmidePalladiumCombinatorial chemistryOrganic chemistryCatalysisAlkylFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsChemical Synthesis and Analysis