ol6b02978_si_001.pdf (8.12 MB)
Selective α‑Deuteration of Amines and Amino Acids Using D2O
journal contribution
posted on 2016-11-02, 16:07 authored by Basujit Chatterjee, Varadhan Krishnakumar, Chidambaram GunanathanMonohydrido-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.
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single-crystal X-ray analysiscymeneD 2 Ocatalyzeacidcatalyst loadaminesAmino AcidsD 2 O Monohydrido-bridged rutheniumimine-ligated rutheniumSelectivedeuterium oxidedeuterium sourcedrug moleculesmigrationimine ligandDeuterationactivationformationβ- Hydride eliminationamine functionalityamide ligand resultsdeuteration-μ-CldeuterideAmineα- CH 2 protonsMechanistic investigations
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