Magnesium-Mediated Cross-Electrophile Couplings of Aryl 2-Pyridyl Esters with Aryl Bromides for Ketone Synthesis through In Situ-Formed Arylmagnesium Intermediates
Xiaowei Han, Yuan He, Chao Gui, Xue‐Qiang Chu, Xuefei Zhao, Xu‐Hong Hu, Xiaocong Zhou, Weidong Rao, Zhi‐Liang Shen
Abstract
Aryl 2-pyridyl esters could efficiently undergo cross-electrophile couplings with aryl bromides with the aid of magnesium as a reducing metal in the absence of a transition-metal catalyst, leading to the unsymmetrical diaryl ketones in modest to good yields with wide functionality compatibility. In addition, the reaction could be easily scaled up and applied in the late-stage modification of biologically active molecules. Preliminary mechanistic study showed that the coupling reaction presumably proceeds through the in situ formation of arylmagnesium reagents as key intermediates.
Topics & Concepts
ElectrophileArylChemistryReagentKetoneMagnesiumCatalysisIn situCoupling reactionMetalCombinatorial chemistryOrganic chemistryAlkylCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms