Copper-Catalyzed Ring-Opening Defluoroborylation of <i>gem</i>-Difluorinated Cyclobutenes: A General Route to Bifunctional 1,3-Dienes and Their Applications
Jie Jia, Fushan Yuan, Zihao Zhang, Xuejiao Song, Fangdong Hu, Ying Xia
Abstract
The exploration of the reactivity of gem-difluorinated small-size rings has continuously drawn attention in recent years but is limited to three-membered carbocycles. Herein we report a copper-catalyzed reaction of gem-fluorinated cyclobutenes with bis(pinacolato)diboron (B2pin2). A sequence of defluoroborylation and a ring-opening process produces B,F-bifunctional 1,3-dienes in a stereoselective manner. The transformation together with the efficient downstream coupling of the boronate and the fluoride moieties collectively constitutes a modular route to highly functionalized and stereocontrolled 1,3-dienes.
Topics & Concepts
ChemistryBifunctionalRing (chemistry)StereoselectivityCatalysisReactivity (psychology)Combinatorial chemistryCopperSequence (biology)FluorideMedicinal chemistryStereochemistryOrganic chemistryInorganic chemistryBiochemistryPathologyMedicineAlternative medicineOrganoboron and organosilicon chemistryFluorine in Organic ChemistryCatalytic Cross-Coupling Reactions