Undirected, Pd-catalysed deuteration of indoles with programmable regioselectivity

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

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

• Working Paper Type: Working Paper
• Deposit Date: Jul 25, 2022
• Publicly Available Date: Jul 26, 2022
• 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