Nickel-Catalyzed Aminoxylation of Inert Aliphatic C(sp3)–H Bonds with Stable Nitroxyl Radicals under Air: One-Pot Route to α‑Formyl Acid Derivatives
journal contributionposted on 23.03.2017, 20:15 by Chunxia Wang, Luoqiang Zhang, Jingsong You
Nickel-catalyzed aminoxylation of an unactivated C(sp3)–H bond with a stable nitroxyl radical has been accomplished for the first time to offer various N-alkoxyamine derivatives, which further enables a one-pot approach to α-formyl acid derivatives. The aminoxylation process reported also provides direct evidence for the oxidative addition of a cyclometallic intermediate with a free radical, which is helpful for the reaction-mechanism study in transition-metal-catalyzed functionalization of inert C(sp3)–H bonds.
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Stable Nitroxyl Radicalsevidenceα- formyl acid derivativesDerivatives Nickel-catalyzed aminoxylationInertone-pot approachNickel-Catalyzed Aminoxylationalkoxyamine derivativesoxidative additionOne-Pot Routeaminoxylation processFormylnitroxylcyclometallicBondunactivatedtransition-metal-catalyzed functionalizationAliphaticreaction-mechanism studybond