Expanded Reaction Scope. Based on the faster rate of product formation as quantified by an increase in kobs and TOFo with DBU and added chloride, as well as the high conversion we observed with 4-ClBzCF3, we explored the scope of the reaction with other challenging aryl halides and nucleophiles (Fig. ). First, under our newly developed conditions we were able to obtain model compound 1 in 74% isolated yield. Though a similar coupling product was obtained in our previous work in 64% isolated yield, these conditions gave highly variable results in the formation of 1, with NMR yields ranging from 9-30% herein. We believe this variability could arise from differing amounts of chloride contamination in the batches of carbonate that were used (See SI, Section 6.7 for further discussion). Next, we were able to couple electron deficient 3chloropyridine and benzyl alcohol to give product 2 in 61% yield. We then investigated the ability of our system to enable coupling with electronically neutral aryl chlorides and successfully isolated the products from the coupling with chlorobenzene (3, 61%) and loratadine (4, 77%), albeit at elevated temperature (70 °C).