Reactivity comparisons with other electrophiles (OFs vs. OTf vs. Br vs. Cl). An interesting comparison was made of the rates of amination of aryl fluorosulfates with other common aryl electrophiles under these relatively mild reaction conditions. Arylation involving two different anilines (1b and 1c) with a variety of aryl electrophiles originating from 1-naphthol were investigated (Table ). Notably, the fluorosulfate was the most reactive electrophile, affording products 1 and 33, respectively, in almost quantitative yield in just after 30 min. Amination of the aryl bromide was slightly slower, giving 1 and 33 in 78 and 68% yields, respectively. Surprisingly, the aryl triflate and aryl chloride only formed trace amounts of these products. It is known that aryl triflates have rates similar to bromides towards oxidative addition to palladium; 67, 68 however, under these reaction conditions, ligand exchange (after the first cycle; vide supra) may be the ratedetermining step. These data suggest that the nature of the leaving group X in the resultant species LnPd(1-naphthyl)X formed after oxidative addition (vide supra) greatly affects the rates of these aminations in water. The aryl fluorosulfate, therefore appear to offer the optimal combination of activity toward oxidative addition and the ability to promote facile nucleophilic attack by the amine substrate in Table . Aminations of various aryl electrophiles under mild conditions. the presence of a weak base like Et3N.