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Selective α‑Deuteration of Amines and Amino Acids Using D2O

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journal contribution
posted on 02.11.2016 by Basujit Chatterjee, Varadhan Krishnakumar, Chidambaram Gunanathan
Monohydrido-bridged ruthenium complex [{(η6-p-cymene)­RuCl}2(μ-H-μ-Cl)] catalyzes (catalyst load: 0.5–1 mol %) α-selective deuteration of primary and secondary amines, amino acids, and drug molecules using deuterium oxide (D2O) as a deuterium source. Mechanistic investigations revealed N–H activation of amines, which was also established by single-crystal X-ray analysis of an intermediate. β-Hydride elimination on amide ligand results in formation of imine-ligated ruthenium intermediate and subsequent 1,3-deuteride migrations to imine ligand leading to the selective deuteration at the α-CH2 protons of amine functionality is proposed.