Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C–H Iodination, Bromination, and Phenylselenation

Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C–H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C–H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.