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Undirected, Pd-catalysed deuteration of indoles with programmable regioselectivity

18 July 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Methods for selective deuterium-incorporation into drug-like molecules have become extremely valuable due to the commercial and biological importance of deuterated compounds. Selective C2-deuteration of indoles currently requires the installation of directing groups on nitrogen. Herein, we report the directing group free, Pd(OAc)2 catalysed, C2-selective deuteration of indoles with CD3CO2D in high yields and selectivity. Slight modification of the reaction conditions also allows selective access to C3- as well as C2-and-C3-deuterated indoles, providing a user-friendly, programmable deuteration scaffold.

Keywords

deuteration
hydrogen isotope exchange
isotopic labelling
homogeneous palladium catalysis
indole
heterocycle drug targets

Supplementary materials

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Experimental procedures and characterization data (PDF)
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Supporting information: Experimental procedures and characterization data (PDF)
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Version History

Jul 18, 2022 Version 1

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-s48dt
D O I: 10.26434/chemrxiv-2022-s48dt [opens in a new tab]

Funding

Science Foundation Ireland
17/RCPhD/3480
European Regional Development Fund
13/RC/2073

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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