Citation: Xianjin Zhu, Yong Liu, Lunyu Ou, Haijun Yang, Hua Fu. Photocatalytic direct oxygen-isotopic labelings of carbonyls in ketones and aldehydes with oxygen-isotopic waters[J]. Chinese Chemical Letters, ;2023, 34(11): 108454. doi: 10.1016/j.cclet.2023.108454 shu

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

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China

fuhua@mail.tsinghua.edu.cn

Received Date: 5 February 2023
Revised Date: 3 April 2023
Accepted Date: 12 April 2023
Available Online: 14 April 2023

Figures(6)

Oxygen-isotopic labelings play important roles in identifying and understanding chemical and biological processes. Direct C=O to C=¹⁸O or C=¹⁷O conversion in a single step leading to labeled compounds can alleviate synthetic burdens without the need for resynthesis. Here we describe a photocatalytic oxygen-isotopic labeling protocol that can efficiently and selectively install ¹⁸O and ¹⁷O on carbonyls of ketones and aldehydes via oxygen isotope exchange with oxygen-isotopic waters (H₂¹⁸O or H₂¹⁷O) 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 NaBH₄ 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.
- Oxygen-isotopic labeling,
- Photocatalysis,
- Oxygen-isotopic waters,
- Compounds containing carbonyls,
- Alkanesulfinates
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