Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates
Russell Shelp, Anthony Ciro, Youge Pu, Rohan R. Merchant, Jonathan M. E. Hughes, Patrick J. Walsh
Abstract
downstream functionalization through a variety of reactions, including a challenging Pd-catalyzed (hetero)arylation that exhibits a broad substrate scope. Together, these methods enable the synthesis of high-value BCP benzylamines which are inaccessible by existing methods. Furthermore, we demonstrate the successful application of these newly developed (hetero)arylation conditions to a variety of challenging tertiary pinacol boronates, including nitrogen-containing heterocycles, 1,1-disubstituted cyclopropanes, and other BCP cores.
Topics & Concepts
BenzylamineBicyclic moleculeSurface modificationChemistryPropellaneBorylationCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryArylPhysical chemistryAlkylOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsOrganometallic Complex Synthesis and Catalysis