Diverting β-Hydride Elimination of a π-Allyl Pd<sup>II</sup> Carbene Complex for the Assembly of Disubstituted Indolines via a Highly Diastereoselective (4 + 1)-Cycloaddition
Zachary D. Tucker, Harrison M. Hill, Andrew Lee Smith, Brandon L. Ashfeld
Abstract
A Pd0-catalyzed formal (4 + 1)-cycloaddition approach to 2,3-disubstituted dihydroindoles is described. The diastereoselective formation of dihydroindoles that is highlighted by a carbene migratory insertion/reductive elimination sequence proceeding via a π-allyl PdII-species compliments existing methods of indoline assembly.
Topics & Concepts
CarbeneChemistryCycloadditionIndolineReductive eliminationHydrideMedicinal chemistryCatalysisCombinatorial chemistryStereochemistryOrganic chemistryHydrogenCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions