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Undirected, Pd-catalysed deuteration of indoles with programmable regioselectivity

Fitzgerald, Liam; McNulty, Rachael; Greener, Andrew; O'Duill, Miriam

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Authors

Liam Fitzgerald

Rachael McNulty

Andrew Greener

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MIRIAM O'DUILL MIRIAM.ODUILL@NOTTINGHAM.AC.UK
Assistant Professor in Chemistry



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.

Citation

Fitzgerald, L., McNulty, R., Greener, A., & O'Duill, M. Undirected, Pd-catalysed deuteration of indoles with programmable regioselectivity

Deposit Date Jul 25, 2022
Publicly Available Date Mar 28, 2024
Keywords deuteration, isotope labelling, homogeneous palladium catalysis, indole, organic synthesis
Public URL https://nottingham-repository.worktribe.com/output/9093442
Publisher URL https://chemrxiv.org/engage/chemrxiv/article-details/62d15a54a7d17edb505c4692

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