Nitrohydroxylation of Olefins with Nitric Acid Using Tridentate NHC–Amidate–Alkoxide Containing Palladium Catalysts

In an attempt to explore the method of nitrohydroxylation which is fairly underdeveloped, our tridentate NHC–amidate–alkoxide containing palladium catalyst was used to nitrohydroxylate a variety of olefins in the presence of nitric acid. These reactions furnished β-nitro alcohols selectively to serve as a direct method for the synthesis of such compounds from various kinds of olefins. Dioxane served as an effective solvent, particularly in conjunction with TFA and AgNO3, which selectively generated the desired products. Vinyl arenes and other olefins produced a wide range of desired products in moderate to good yields.