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

作　　者：Xianjin Zhu Yong Liu Lunyu Ou Haijun Yang Hua Fu 

机构地区：[1]Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology(Ministry of Education),Department of Chemistry,Tsinghua University,Beijing 100084,China

出　　处：《Chinese Chemical Letters》2023年第11期131-136,共6页中国化学快报（英文版）

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).

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.

关 键 词：Oxygen-isotopic labeling Photocatalysis Oxygen-isotopic waters Compounds containing carbonyls Alkanesulfinates 

分 类 号：O62[理学—有机化学]