AI Article Synopsis
- Researchers have identified a new, gentle method for deuterating certain aromatic compounds that involves a keto-enamine tautomeric intermediate.
- The study utilized kinetics and computational analysis to understand the reaction mechanism, highlighting the importance of water molecules in reducing the activation barrier.
- The findings suggest that leveraging tautomeric forms of aromatic compounds can significantly increase their reactivity.
Article 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.
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| http://dx.doi.org/10.1021/acs.joc.5b00539 | DOI Listing |
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