Ruthenium-Catalyzed Hydroxyl-Directed <i>peri</i>-Selective C–H Activation and Annulation of 1-Naphthols with CF<sub>3</sub>–Imidoyl Sulfoxonium Ylides for the Synthesis of 2-(Trifluoromethyl)-2,3-dihydrobenzo[<i>de</i>]chromen-2-amines
Zuguang Yang, Jianhua Tang, Zhengkai Chen, Xiao‐Feng Wu
Abstract
A ruthenium-catalyzed peri-selective C–H activation and annulation of 1-naphthols with CF3-substituted imidoyl sulfoxonium ylides that uses hydroxyl as a weakly coordinating directing group is disclosed. The strategy provides a facile and practical route to diverse trifluoromethyl-containing 2,3-dihydrobenzo[de]chromen-2-amines with high efficiency. Notable advantages of this protocol include readily available materials, excellent regioselectivity, good functional group compatibility, and scalability.
Topics & Concepts
AnnulationChemistryRegioselectivityTrifluoromethylCatalysisRutheniumCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsFluorine in Organic ChemistryCyclopropane Reaction Mechanisms