Facilitating Rh-Catalyzed C–H Alkylation of (Hetero)arenes and 6-Arylpurine Nucleosides (Nucleotides) with Electrochemistry
Qi‐Liang Yang, Ying Liu, Lei Liang, Zhi-Hao Li, Gui‐Rong Qu, Hai‐Ming Guo
Abstract
-C-H alkylation of (hetero)arenes via rhodium catalysis under mild conditions is described. This approach features mild conditions with high levels of regio- and monoselectivity that tolerate a variety of aromatic and heteroaromatic groups and offers a widely applicable method for late-stage diversification of complex molecular architectures including tryptophan, estrone, diazepam, nucleosides, and nucleotides. Alkyl boronic acids and esters and alkyl trifluoroborates are demonstrated as suitable coupling partners. The isolation of key rhodium intermediates and mechanistic studies provided strong support for a rhodium(III/IV or V) regime.
Topics & Concepts
AlkylationNucleotideCatalysisElectrochemistryChemistryCombinatorial chemistryStereochemistryOrganic chemistryBiochemistryElectrodePhysical chemistryGeneCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisRadical Photochemical Reactions