Site‐Selective (<i>Z</i>)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling
Mireia Pujol, Ricardo J. Maza, Oriol Salvadó, Jorge J. Carbó, Elena Fernández
Abstract
Abstract 1,1‐Diborylalkenes can be transformed into ( Z )‐skipped dienes through Cu I ‐phosphine catalyzed allylic coupling reactions. The energetically preferred formation of ( Z )‐α‐borylalkenyl copper (I) species and the subsequent nucleophilic attack, explains the stereoselective nucleophilic substitution with allyl bromides. The eventual treatment of ( Z )‐skipped dienes with NaO t Bu promotes cyclization/aromatization patterns via enyne intermediates.
Topics & Concepts
Allylic rearrangementCopperNucleophileCoupling (piping)ChemistryCrystallographyStereochemistryMaterials scienceMetallurgyOrganic chemistryCatalysisOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsOrganometallic Complex Synthesis and Catalysis