title: Deuteration of Aromatic Rings under Very Mild Conditions through Keto-Enamine Tautomeric Amplification.
abstract: We have discovered a surprising, mild method for deuteration of select aromatic compounds that is facilitated by a keto-enamine tautomeric intermediate. The mechanism of the reaction has been studied using kinetics experiments and detailed computational analysis. It was found that a chain of water molecules has a substantial role in lowering the activation barrier to the tautomerization-enhanced deuteration reaction. Our results demonstrate that tautomeric forms of aromatic molecules can be exploited to bring about enhanced reactivity.
authors.affiliation: †Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada.
authors.forename: S Hessam M
authors.initials: SH
authors.lastname: Mehr
authors.affiliation: ‡Center for Liberal Arts, Meiji Gakuin University, Yokohama 244-8539, Japan.
authors.forename: Katsuya
authors.initials: K
authors.lastname: Fukuyama
authors.affiliation: †Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Bishop
authors.affiliation: §Department of Scienze and LaSCaMM of INSTM, Università della Basilicata, 85100 Potenza, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Lelj
authors.affiliation: †Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada.
authors.forename: Mark J
authors.initials: MJ
authors.lastname: MacLachlan