Palladium-Catalyzed Denitrative α-Arylation of Heteroarenes with Nitroarenes via C–H and C–NO<sub>2</sub> Bond Activations
Jiaxin Yao, Yuxuan Xiao, Haiyan Li, Xun Yang, Jiahui Du, Ying Yin, Feng Lin, Wengui Duan, Lin Yu
Abstract
A general approach for the α-arylation of heteroarenes with nitroarenes via denitrative coupling is reported for the first time. Various heteroarenes, including derivatives of furan, benzofuran, pyrrole, indole, thiophene, and benzothiophene, can be arylated at the α-position in moderate to good yields. Mechanistic studies demonstrate that the reaction proceeds via a CMD pathway, with C-H bond activation as the rate-determining step. Furthermore, the scalability and applicability in the synthesis of a drug molecule exemplify the utility of this protocol.
Topics & Concepts
BenzothiopheneChemistryBenzofuranIndole testPyrroleFuranThiopheneCatalysisCombinatorial chemistryPalladiumMoleculeComputational chemistryStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques