Selective α-Deuteration of Amines and Amino Acids Using D2O.
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-CH2protons of amine functionality is proposed.
School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI , Bhubaneswar 752 050, India.
Basujit
B
Chatterjee
School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI , Bhubaneswar 752 050, India.
Varadhan
V
Krishnakumar
School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI , Bhubaneswar 752 050, India.
Chidambaram
C
Gunanathan
D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D017666:Deuterium Oxide / Q000737:chemistry*; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
D000588:Amines; D000596:Amino Acids; D004364:Pharmaceutical Preparations; D012428:Ruthenium; D017666:Deuterium Oxide