Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems

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.