Palladium-Catalyzed C(sp<sup>3</sup>)–H Nitrooxylation with <i>tert</i>-Butyl Nitrite and Molecular Oxygen
Bo Li, Ye‐Qiang Han, Yang Xu, Bing‐Feng Shi
Abstract
Herein, we report a Pd(II)-catalyzed nitrooxylation of unactivated methyl C(sp3)–H bonds using commercial available and easily manageable tert-butyl nitrite as the precursor of ONO2 radical under aerobic conditions. Environmentally benign molecular oxygen is used to initiate the generation of active radical reactant; it is also used as the terminal oxidant. A broad range of nitrooxylated aliphatic carboxamides were prepared in moderate to good yields under mild conditions.
Topics & Concepts
ChemistryCatalysisPalladiumNitriteOxygenMolecular oxygenMedicinal chemistryOrganic chemistryNitrateCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions