摘要
Oxygen-isotopic labelings play important roles in identifying and understanding chemical and biological processes.Direct C=O to C=^(18)O or C=^(17)O conversion in a single step leading to labeled compounds can alleviate synthetic burdens without the need for resynthesis.Here we describe a photocatalytic oxygenisotopic labeling protocol that can efficiently and selectively install ^(18)O and ^(17)O on carbonyls of ketones and aldehydes via oxygen isotope exchange with oxygen-isotopic waters(H_(2)^(18)O or H_(2)^(17)O)as the sources of oxygen isotopes,in which light and oxygen-enabled sodium alkanesulfinates catalyzed this process.This strategy was extended to the in-situ formed ketones from the photocatalytic aerobic oxidation of alkyl arenes and secondary alcohols.Furthermore,reduction of the oxygen-isotopically labeled aldehydes with NaBH_(4) provided the corresponding oxygen-isotopically labeled primary alcohols.We believe that the oxygen-isotopically labeling method will be widely used in chemistry,biology and medicine fields.
基金
supported by Natural Science Foundation of Beijing Municipality(No.2222011)
National Natural Science Foundation of China(No.22077074)
China Postdoctoral Science Foundation(No.2021M701869).