Date of Award
Bachelor of Science
The introduction of an aryl group a to a carbonyl is a useful step in the preparation of a variety of biologically interesting compounds. The palladium-catalyzed a-arylation of ketones and esters, through their enolates, has received a great deal of attention lately. Despite these efforts, cyclopentanones remain one of the most difficult classes ofketones to arylate. Many of these methods suffer from the limitation of the relatively basic reaction conditions needed in order to prepare the enolate nucleopbiles insitu. The direct palladium-catalyzed α-arylation of enamines as an alternative route to αaryl ketones bas received very little attention and might be a way to circumvent the strong base problem. In an effort to overcome this problem a method for the direct palladium-cawyzed a-arylation of unactivated enamines of cyclopentanone through the use of high-throughput screening was developed. When applied to reactions with 1- pyrollidino-1-cylcopentane and various iodobenzene derivatives we have achieved yields of above 90% for the arylated cyclopentanone in all successful cases at a one mmol scale.
Gehring, Kristina M., "α-Arylation of cyclopentanone : palladium-catalyzed coupling of enamines and aryliodides & n-acyloxazines as novel bicyclic Weinreb amides" (2006). Honors Theses. 2094.