Electrochemical Deoxygenative Hydrogenation and Deuteration of Aldehydes/Ketones by Protic Acids in Water
Zhihui Sun, Ruixue Ji, Jintao Wu, Jianyou Zhao, Fang Fang, Fan Wang, Chao Jiang, Zhong‐Quan Liu
Abstract
Abstract We report herein a modified Clemmensen reduction. When reacted with aqueous H(D)Cl in an undivided cell, aliphatic and aromatic aldehydes and ketones undergo deoxygenative hydrogenation and deuterization to give hydrocarbons and deuterocarbons. The general features of this transformation are: 1) H + /D + as the sources of H/D; 2) mild reaction conditions (room temperature, open flask, CH 3 CN and water as cosolvent); 3) easily scaled‐up to 100 grams. A series of D‐labeled drugs were synthesized by this method. magnified image
Topics & Concepts
ChemistryAqueous solutionElectrochemistryOrganic chemistryMedicinal chemistryPhysical chemistryElectrodeChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisMass Spectrometry Techniques and Applications