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Regioselective and Stereospecific Deuteration of Bioactive Aza Compounds by the Use of Ruthenium Nanoparticles
Author(s) -
Pieters Grégory,
Taglang Céline,
Bonnefille Eric,
Gutmann Torsten,
Puente Céline,
Berthet JeanClaude,
Dugave Christophe,
Chaudret Bruno,
Rousseau Bernard
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201307930
Subject(s) - regioselectivity , chemistry , ruthenium , stereocenter , stereospecificity , yield (engineering) , isotopic labeling , alkyl , combinatorial chemistry , molecule , enantiomer , nanoparticle , organic chemistry , catalysis , nanotechnology , enantioselective synthesis , materials science , metallurgy
An efficient H/D exchange method allowing the deuteration of pyridines, quinolines, indoles, and alkyl amines with D 2 in the presence of Ru@PVP nanoparticles is described. By a general and simple procedure involving mild reaction conditions and simple filtration to recover the labeled product, the isotopic labeling of 22 compounds proceeded in good yield with high chemo‐ and regioselectivity. The viability of this procedure was demonstrated by the labeling of eight biologically active compounds. Remarkably, enantiomeric purity was conserved in the labeled compounds, even though labeling took place in the vicinity of the stereogenic center. The level of isotopic enrichment observed is suitable for metabolomic studies in most cases. This approach is also perfectly adapted to tritium labeling because it uses a gas as an isotopic source. Besides these applications to molecules of biological interest, this study reveals a rich and underestimated chemistry on the surface of ruthenium nanoparticles.