Selective deuteration of heterocycle N-oxides via iridium-catalyzed hydrogen isotope exchange

Tools

Owens, Philippa and Smith, Blair and Lindsay, David and Campos, Sebastien and Kerr, William J (2023) Selective deuteration of heterocycle N-oxides via iridium-catalyzed hydrogen isotope exchange. Synthesis, 55 (21). pp. 3644-3651. ISSN 0039-7881 (https://doi.org/10.1055/a-2088-4302)

[thumbnail of Owens-etal-Synthesis-2023-Selective-deuteration-of-heterocycle-N-oxides]
Preview
 Text. Filename: Owens_etal_Synthesis_2023_Selective_deuteration_of_heterocycle_N_oxides.pdf
Accepted Author Manuscript
License: Creative Commons Attribution 4.0 logo
Download (1MB)| Preview

Abstract

An iridium(I) N-heterocyclic carbene/phosphine complex has been applied to the C-H activation and hydrogen isotope exchange of quinoline N-oxides. The isotope labelling proceeds under exceptionally low catalyst loadings of 0.25 mol%, and delivers products with high levels of deuterium incorporation selectively at the C8 position. A broad substrate scope is demonstrated, with the method tolerant of electron-poor and -rich substrates, and of substitution adjacent to the site of C-H activation. The isotope label is fully retained under standard deoxygenation conditions to give the corresponding labelled quinoline, and the labelling and deoxygenation can be combined in a one-pot procedure.

ORCID iDs

Owens, Philippa ORCID logoORCID: https://orcid.org/0000-0002-9369-2899, Smith, Blair, Lindsay, David ORCID logoORCID: https://orcid.org/0000-0003-4498-5094, Campos, Sebastien and Kerr, William J ORCID logoORCID: https://orcid.org/0000-0002-1332-785X;
CORE (COnnecting REpositories)