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.