3-Alkyl-2-pyridyl Directing Group-Enabled C2 Selective C–H Silylation of Indoles and Pyrroles via an Iridium Catalyst
Hui Sun, Yi An Cheng, Houyun Teng, Xiaoqi Chen, Xiaokang Niu, Hao Yang, Yu‐Ming Cui, Li‐Wen Xu, Lei Yang
Abstract
An iridium-catalyzed, directing group-enabled site selective intra- and intermolecular silylation of indoles and pyrroles with hydrosilanes has been developed under ligand-free conditions. Fine-tuning of the removable 3-alkyl-2-pyridyl directing group was found to be crucial for achieving high yields for C2-silylated indole and pyrrole products. Moreover, the scalability was demonstrated, and further transformations of the silylation products were achieved.
Topics & Concepts
IridiumChemistrySilylationAlkylCatalysisPyrroleLigand (biochemistry)Indole testGroup (periodic table)Intermolecular forceCombinatorial chemistryOrganic chemistryMedicinal chemistryMoleculeReceptorBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis