Programmable Deuteration of Indoles via Reverse Deuterium Exchange

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

Abstract

Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allows access to C2, C3, or C2- and C3-deuterated indoles under mild, user-friendly conditions. The C2-deuterated indoles are accessed using a reverse hydrogen isotope exchange strategy which represents the first non-directed C2-deuteration of indoles.

Citation

Fitzgerald, L. S., McNulty, R. L., Greener, A., & O'Duill, M. L. (2023). Programmable Deuteration of Indoles via Reverse Deuterium Exchange. Journal of Organic Chemistry, 88(15), 10772-10776. https://doi.org/10.1021/acs.joc.3c00819

• Journal Article Type: Article
• Acceptance Date: Jul 11, 2023
• Online Publication Date: Jul 21, 2023
• Publication Date: Aug 4, 2023
• Deposit Date: Jul 31, 2023
• Publicly Available Date: Aug 1, 2023
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 88
• Issue: 15
• Pages: 10772-10776
• DOI: https://doi.org/10.1021/acs.joc.3c00819
• Keywords: Hydrogen isotopes, Indoles, Palladium, Pharmaceuticals, Solvents
• Public URL: https://nottingham-repository.worktribe.com/output/23488658
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.joc.3c00819