Shifted Selectivity in Protonation Enables the Mild Deuteration of Arenes Through Catalytic Amounts of Bronsted Acids in Deuterated Methanol

Fischer O, Hubert A, Heinrich M (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Journal of Organic Chemistry American Chemical Society

Book Volume: 85

Pages Range: 11856-11866

Journal Issue: 18

DOI: 10.1021/acs.joc.0c01604

Abstract

Taking advantage of the "differentiating effect" of the solvent methanol, deuterations of electron-rich aromatic systems can be carried out under mild acid catalysis and thus under far milder conditions than known so far. The exceptional functional group tolerance observed under the optimized conditions, which even includes highly acid-labile groups, results from a hitherto unexploited shifted selectivity in protonation, and enabled simple and straightforward access to complex deuterium-labeled compounds.

Authors with CRIS profile

Oliver Fischer Professur für Pharmazeutische Chemie Markus Heinrich Professur für Pharmazeutische Chemie

How to cite

APA:

Fischer, O., Hubert, A., & Heinrich, M. (2020). Shifted Selectivity in Protonation Enables the Mild Deuteration of Arenes Through Catalytic Amounts of Bronsted Acids in Deuterated Methanol. Journal of Organic Chemistry, 85(18), 11856-11866. https://doi.org/10.1021/acs.joc.0c01604

MLA:

Fischer, Oliver, Anja Hubert, and Markus Heinrich. "Shifted Selectivity in Protonation Enables the Mild Deuteration of Arenes Through Catalytic Amounts of Bronsted Acids in Deuterated Methanol." Journal of Organic Chemistry 85.18 (2020): 11856-11866.

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