Nickel‐Catalyzed N‐Arylation of Fluoroalkylamines
Ryan T. McGuire, Arun A. Yadav, Mark Stradiotto
Abstract
The Ni-catalyzed N-arylation of β-fluoroalkylamines with broad scope is reported for the first time. Use of the air-stable pre-catalyst (PAd2-DalPhos)Ni(o-tol)Cl allows for reactions to be conducted at room temperature (25 °C, NaOtBu), or by use of a commercially available dual-base system (100 °C, DBU/NaOTf), to circumvent decomposition of the N-(β-fluoroalkyl)aniline product. The mild protocols disclosed herein feature broad (hetero)aryl (pseudo)halide scope (X=Cl, Br, I, and for the first time phenol-derived electrophiles), encompassing base-sensitive substrates and enantioretentive transformations, in a manner that is unmatched by any previously reported catalyst system.
Topics & Concepts
CatalysisElectrophileAnilineNickelHalideChemistryArylCombinatorial chemistryPhenolDecompositionBase (topology)Medicinal chemistryOrganic chemistryMathematicsAlkylMathematical analysisFluorine in Organic ChemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods