Organic Base Enabled Nickel-Catalyzed Mono-alpha-Arylation of Feedstock Solvents

We report on our successful development of the first metal-catalyzed mono-alpha-arylation of carbonyl compounds employing a soluble organic base. The scope of these Ni/DalPhos-catalyzed transformations encompasses a range of (hetero)aryl halides (Cl, Br, I) and phenol-derived electrophiles (sulfonates, carbonates, carbamates, sulfamates), including active pharmaceutical ingredients (chloroquine, clozapine), in combination with the typically problematic feedstock small molecule substrates acetone, dimethylacetamide, and for the first time with any metal catalyst/base, ethyl acetate.