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- Title
Iridium-Catalysed ortho-Directed Deuterium Labelling of Aromatic Esters_An Experimental and Theoretical Study on Directing Group Chemoselectivity.
- Authors
Devlin, Jennifer; Kerr, William. J.; Lindsay, David M.; McCabe, Timothy J. D.; Reid, Marc; Tuttle, Tell
- Abstract
Herein we report a combined experimental and theoretical study on the deuterium labelling of benzoate ester derivatives, utilizing our developed iridium N-heterocyclic carbene/phosphine catalysts. A range of benzoate esters were screened, including derivatives with electron-donating and -withdrawing groups in the para- position. The substrate scope, in terms of the alkoxy group, was studied and the nature of the catalyst counter-ion was shown to have a profound effect on the efficiency of isotope exchange. Finally, the observed chemoselectivity was rationalized by rate studies and theoretical calculations, and this insight was applied to the selective labelling of benzoate esters bearing a second directing group.
- Subjects
IRIDIUM catalysts; DEUTERIUM; CHEMOSELECTIVITY; CARBENES; CATALYSTS; PHOSPHINE; ELECTRON donors; BENZOATES
- Publication
Molecules, 2015, Vol 20, Issue 7, p11676
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules200711676