Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems
Roman Kleinmans, Omar Apolinar, Joseph Derosa, Malkanthi K. Karunananda, Zi‐Qi Li, Van Tran, Steven R. Wisniewski, Keary M. Engle
Abstract
A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.
Topics & Concepts
ChemistryCatalysisSubstrate (aquarium)ArylCombinatorial chemistryProduct (mathematics)Organic chemistryMathematicsAlkylGeometryGeologyOceanographyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms