Chen, research group and collaborator of Yan Xiaoyu, Renmin University of China: hydrogen deuterium exchange reaction of aldehydes catalyzed by intermediate carbene (MIC)

Deuterium labeled compounds are widely used in the fields of organic reaction mechanism research, analysis and test, materials science, life science and medicine Isotope dilution mass spectrometry (IDMS) based on deuterium labeled compounds has been widely used in quantitative analysis, which is less affected by matrix effect, and has the advantages of rapidity, accuracy, high sensitivity and good repeatability Deuterium labeled drug molecules are also widely used in drug metabolism process analysis and clinical pharmacokinetic study It is an important method to synthesize deuterium labeled compounds through the activation of C-H bond and the exchange reaction of hydrogen and deuterium Selective hydrogen deuterium exchange, especially on active alkyl, benzyl, heteroatom, aromatic ring and olefin, has made a series of significant progress in recent years However, there are few studies on the hydrogen deuterium exchange reaction of aldehydes At present, the research is limited to the iridium / ruthenium catalyzed hydrogen deuterium exchange reaction of aromatic aldehydes On the other hand, it has been more than half a century since NHC formed Breslow intermediate with aldehydes to realize the polar inversion and activation of aldehydes However, the simplest reaction form of NHC catalyzed exchange of aldehydes and deuterium has not yet been realized The main reason lies in the inability to block benzoin condensation reaction and the lack of reversible research on activation Recently, Yan Xiaoyu, Department of chemistry, Renmin University of China, cooperated with Professor Jean Bouffard of Lihua women's University of Korea and Professor guy Bertrand of the University of California, San Diego, USA, based on Series 1 and 2 developed by the research group, 3-triazole carbene (MIC), through blocking benzoin condensation reaction, realizes hydrogen deuterium exchange reaction of aldehydes under nonmetal catalysis The reaction has very good substrate universality and functional group compatibility (Figure 1) This work was recently published in the cell sister journal chem (CHEM, 2019, 5, 2484-2494) The first author is Liu Wei, Ph.D student, Department of chemistry, Renmin University of China.