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A chemodivergent copper-catalyzed ring opening of cycloketone oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of γ- and δ-acyloxylated, alkoxylated, and hydroxylated nitriles while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxime also proceeded well under the established conditions.
Ai et al. (Wed,) studied this question.