A new method of oxidative C-H bond functionalization is presented. Coordinating heteroatoms within the substrates are used to direct the palladium catalyst to a specific carbon-hydrogen bond, allowing regiospecific C-H activation to take place. A variety of oxidants are effective in oxidizing the resulting palladium complex to a high energy Pd(IV) species, from which reductive elimination of the desired functionality can take place. Iodobenzene diacetate and N-halosuccinimides have been found to be particularly good oxidants, and lead to acetoxylation or halogenation of a variety of organic substrates under mild conditions. A number of directing groups can be used to achieve the desired regioselectivity, including pyridines, oxime ethers, azo linkages, and amides, and both sp² and sp³ C-H bonds undergo facile functionalization with selectivity that is often complimentary to traditional organic methodology.