Exploring the Electronic and Steric Effects of Hemilabile (P^N) Ligands in Redox Gold Catalysis: Application to the Cross-Coupling Reaction of Aliphatic Amines with Aryl Iodides
Urvashi Urvashi, Saurabh Rai, Gaurav Shukla, Nisha Nisha, Nitin T. Patil
Abstract
Herein, we report 17 new (P^N) ligands for redox gold catalysis, featuring various substituents at −C4, −C5, and −C6 of the aryl ring and nitrogen handle. Rate kinetics experiments revealed that electron-rich substituents at −C4 and −C5 positions of the aryl ring enhanced the rate of oxidative addition of Au(I) with C(sp 2 )–Br bonds compared to electron-poor substituents. Further, we report an unprecedented gold-catalyzed arylation of aliphatic amines using an electronically rich ligand ( L6 ) with an −OMe group at the −C5 position.
Topics & Concepts
ChemistrySteric effectsArylCatalysisRedoxCoupling reactionCoupling (piping)Combinatorial chemistryElectronic effectPhotochemistryOrganic chemistryMedicinal chemistryMechanical engineeringEngineeringAlkylCatalytic Alkyne ReactionsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis