Ligand- and Counterion-Assisted Phenol <i>O</i>-Arylation with TMP-Iodonium(III) Acetates
Kotaro Kikushima, Naoki Miyamoto, Kazuma Watanabe, Daichi Koseki, Yasuyuki Kita, Toshifumi Dohi
Abstract
High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.
Topics & Concepts
ChemistryReactivity (psychology)CounterionPhenolLigand (biochemistry)Steric effectsElectrophileAlcoholMedicinal chemistryOrganic chemistryCombinatorial chemistryIonCatalysisPathologyAlternative medicineMedicineReceptorBiochemistryOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions