Copper-Catalyzed Aerobic C(<i>sp</i>³)–H Oxidation of β-(Alkoxy)imino Carbonyl Compounds

Abstract

Direct oxidation of the C(sp 3 )-H bond of β-(alkoxy)imino carbonyl compounds using copper acetate and molecular oxygen has been established. The protocol features a broad substrate scope and generates 1-imino-2,3-dicarbonyls in good to excellent yields.

Synthesis of oxime ethers via a formal reductive O–H bond insertion of oximes to α-keto esters

“…Intrigued by the attractive reactivity of the KRAs and motivated by the challenging goal of synthesizing oxime ethers, we hypothesized that a trivalent phosphorous reagent-mediated diazo-free O–H bond insertion between oximes and α-keto esters would provide a simple and practical protocol to construct oxime ethers. 13 This methodology would demonstrate broad substrate scope, including nitrogen-containing aromatic rings such as pyridines and quinolines, due to the absence of highly reactive free carbene species.…”