Photocatalytic direct oxygen-isotopic labelings of carbonyls in ketones and aldehydes with oxygen-isotopic waters

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.