Bridge Cross-Coupling of Bicyclo[1.1.0]butanes
Ryan E. McNamee, Ayan Dasgupta, Kirsten E. Christensen, Edward A. Anderson
Abstract
High Resolution Image Download MS PowerPoint Slide Bicyclo[1.1.0]butanes (BCBs) have gained growing popularity in “strain release” chemistry for the synthesis of four-membered-ring systems and para - and meta -disubstituted arene bioisosteres as well as applications in chemoselective bioconjugation. However, functionalization of the bridge position of BCBs can be challenging due to the inherent strain of the ring system and reactivity of the central C–C bond. Here we report the first late-stage bridge cross-coupling of BCBs, mediated by directed metalation/palladium catalysis.
Topics & Concepts
ChemistryBicyclic moleculeBridge (graph theory)Ring (chemistry)Reactivity (psychology)MetalationBioconjugationCoupling (piping)StereochemistryCombinatorial chemistryOrganic chemistryMaterials scienceAlternative medicineMetallurgyPathologyInternal medicineMedicineCyclopropane Reaction MechanismsCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods