Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing N-Heterocycles via Transforming C–H to C–OH Bonds

Abstract

We developed a molecular-oxygen-mediated multicomponent oxidative cyclization strategy to synthesize Nheterocycles containing tertiary alcohol units via the formation of key C−OH bonds and quaternary carbon centers. This formal [3 + 2 + 1] annulation offers a green and sustainable alternative for the de novo C−OH bond formation, using O 2 as both the oxidant and oxygen source under metal-and catalyst-free conditions. Notably, continuous [1,5]-hydrogen transfer together with excess alcohols promotes the formation of C−OH-bearing products. Additionally, the generation of quaternary carbon centers inhibits the conversion of C−OH bonds to C�O bonds, thus stabilizing the desired products.