Mehr, S. H. M. , Fukuyama, K., Bishop, S., Lelj, F. and MacLachlan, M. J. (2015) Deuteration of aromatic rings under very mild conditions through keto-enamine tautomeric amplification. Journal of Organic Chemistry, 80(10), pp. 5144-5150. (doi: 10.1021/acs.joc.5b00539) (PMID:25906051)
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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.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Mehr, Dr Hessam |
| Authors: | Mehr, S. H. M., Fukuyama, K., Bishop, S., Lelj, F., and MacLachlan, M. J. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Published Online: | 23 April 2015 |
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