Transition Metal‐Free <i>O</i>‐Arylation of <i>N</i>‐Alkoxybenzamides Enabled by Aryl(trimethoxyphenyl)iodonium Salts
Elghareeb E. Elboray, Taeho Bae, Kotaro Kikushima, Yasuyuki Kita, Toshifumi Dohi
Abstract
Abstract Herein, we develop a metal catalyst‐free protocol for O ‐arylation of benzamide hydroxamate esters. The chemoselective O ‐ versus N ‐arylation of the amides was tuned by varying the electronic and/or steric properties of the diaryliodonium salt and/or the substrate. The O ‐arylation reaction would preferentially occur for sterically and electronically diverse substrates. This study, which reveals the possibility of substituent‐ and reagent‐controlled chemoselectivity, with diaryliodonium salts might attract interest in the area of hypervalent iodine chemistry.
Topics & Concepts
ChemistryHypervalent moleculeChemoselectivitySteric effectsArylTransition metalBenzamideReagentCatalysisSubstituentSalt (chemistry)Combinatorial chemistrySubstrate (aquarium)Organic chemistryMedicinal chemistryAlkylOceanographyGeologyCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions