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Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O‑Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

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journal contribution
posted on 03.01.2018, 16:08 by Wenying Ai, Yaqian Liu, Qian Wang, Zhonglin Lu, Qiang Liu
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.