Triazabicyclodecene: an effective isotope exchange catalyst in CDCl(3).
We describe the first effective H/D exchange reaction with acidic substrates in CDCl(3) at room temperature. The particularly mild reaction conditions involved (solvent, base, and temperature) allow the chemoselective deuteration of ketones over esters. An NMR study was conducted with the aim of rationalizing the results obtained in the presence of TBD as catalyst.
Sabot
Cyrille
C
Laboratoire de Synthèse Bio-Organique, UMR 7175/LC1-CNRS, Université Louis Pasteur de Strasbourg, B.P. 60024, 67401 Illkirch cedex, France.
Kumar
Kanduluru Ananda
KA
Antheaume
Cyril
C
Mioskowski
Charles
C
D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D003903:Deuterium; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure
D001372:Aza Compounds; D006574:Heterocyclic Compounds, 2-Ring; D006843:Hydrocarbons, Chlorinated; D007659:Ketones; D003903:Deuterium