Catalytic Highly Regioselective C–H Oxygenation Using Water as the Oxygen Source: Preparation of <sup>17</sup>O/<sup>18</sup>O-Isotope-Labeled Compounds
Daiki Doiuchi, Tatsuya Uchida
Abstract
We found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of PhI(OOCR)2 and can be used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C–H oxygenation. Ru(bpga)/PhI(OOCR)2/H2O system, sterically less bulky methinic and methylenic C–H bonds in various compounds can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as d-[3-17O/18O]-mannose can be prepared in a multigram scale.
Topics & Concepts
ChemistryCatalysisOxygenSteric effectsRegioselectivityHydrolysisOxygen-18RutheniumKinetic isotope effectOxygen-17Oxygen atomMoleculeOxygenationMedicinal chemistryInorganic chemistryStereochemistryOrganic chemistryDeuteriumBiologyQuantum mechanicsNuclear magnetic resonanceEcologyPhysicsMetal-Catalyzed Oxygenation MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods