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Deuteration of Aromatic Rings under Very Mild Conditions through Keto-Enamine Tautomeric Amplification

TitleDeuteration of Aromatic Rings under Very Mild Conditions through Keto-Enamine Tautomeric Amplification
Publication TypeJournal Article
Year of Publication2015
AuthorsS. Mehr, HM, Fukuyama, K, Bishop, S, Lelj, F, MacLachlan, MJ
JournalJournal of Organic Chemistry
Volume80
Pagination5144-5150
ISSN0022-3263
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.

URL<Go to ISI>://WOS:000354908500032
DOI10.1021/acs.joc.5b00539