Palladium-Catalyzed Dearomative Heck/Suzuki Coupling of C2-Deuterated or C2-Nonsubstituted Indoles
Wei‐Yang Gao, Gao-Yang Yu, Yanyu Li, Ren‐Xiao Liang, Xin Hong, Yi‐Xia Jia
Abstract
A palladium-catalyzed dearomative diarylation of C2-deuterated or C2-nonsubstituted indoles through domino Heck/Suzuki coupling is established. Relying on electron-deficient phosphite ligand, side reactions including intermolecular Suzuki coupling and intramolecular C-D/H arylation are inhibited and a wide range of 2,3-diarylated indolines bearing vicinal tertiary stereocenters including deuterated ones are afforded in moderate to excellent yields (up to 94%) and excellent diastereoselectivities (>20:1). The catalyst loading can be lowered to 0.02 mol % at elevated temperature.
Topics & Concepts
ChemistryStereocenterIntramolecular forcePalladiumDominoCatalysisDeuteriumSuzuki reactionHeck reactionLigand (biochemistry)Coupling (piping)Combinatorial chemistryOrganic chemistryEnantioselective synthesisReceptorEngineeringPhysicsQuantum mechanicsMechanical engineeringBiochemistryChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions