Iron‐Catalyzed Borylation of Propargylic Acetates for the Synthesis of Multisubstituted Allenylboronates
Aitor Bermejo‐López, Wei‐Jun Kong, Pedro J. Tortajada, Daniels Posevins, Belén Martín‐Matute, Jan‐E. Bäckvall
Abstract
Abstract A novel iron‐catalyzed borylation of propargylic acetates leading to allenylboronates has been developed. The method allows the preparation of a variety of di‐, tri‐ and tetrasubstituted allenylboronates at room temperature with good functional group compatibility. Stereochemical studies show that an anti ‐S N 2’ displacement of acetate by boron occurs; this also allows transfer of chirality to yield enantiomerically enriched allenylboronates. The synthetic utility of this protocol was further substantiated by transformations of the obtained allenylboronates including oxidation and propargylation.
Topics & Concepts
BorylationChemistryCatalysisBoronYield (engineering)Compatibility (geochemistry)Combinatorial chemistryChirality (physics)Organic chemistryMedicinal chemistryMaterials scienceMetallurgyPhysicsAlkylNambu–Jona-Lasinio modelQuantum mechanicsArylChiral symmetry breakingQuarkComposite materialCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistryCatalytic Cross-Coupling Reactions