Visible Light-Induced α-C(sp<sup>3</sup>)–H Acetalization of Saturated Heterocycles Catalyzed by a Dimeric Gold Complex
Xiaojia Si, Lumin Zhang, Zuozuo Wu, Matthias Rudolph, Abdullah M. Asiri, A. Stephen K. Hashmi
Abstract
Saturated heterocyclic acetals are useful fragments in organic synthesis and other fields. Herein, C(sp3)–H dehydrogenative cross-couplings of ethers, tetrahydrothiophenes, and pyrrolidines were achieved under visible light irradiation by using iodobenzene and an in situ-formed gold complex. The broad functional group compatibility and substrate scope indicate that our strategy is a promising way to synthesize acetal analogues. The method was successfully applied in late-stage modifications of bioactive molecules. Gram scale syntheses and mechanistic studies are also presented.
Topics & Concepts
ChemistryCatalysisMedicinal chemistryPhotochemistryStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsCatalytic Alkyne Reactions