Regioselective partial hydrogenation and deuteration of tetracyclic (Hetero)aromatic systems using a simple heterogeneous catalyst

Kehoe, Roberta A.; Lowry, Amy; Light, Mark E.; Jones, David J.; Byrne, Peter; McGlacken, Gerard P.

Regioselective partial hydrogenation and deuteration of tetracyclic (Hetero)aromatic systems using a simple heterogeneous catalyst

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Supplementary information

Chemistry A European J - 2024 - Kehoe - Regioselective Partial Hydrogenation and Deuteration of Tetracyclic Hetero.pdf(3.29 MB)

Published version

Date

2024-11-12

Authors

Kehoe, Roberta A.

Lowry, Amy

Light, Mark E.

Jones, David J.

Byrne, Peter

McGlacken, Gerard P.

Publisher

Wiley

Published Version

https://doi.org/10.1002/chem.202400102

Abstract

The introduction of added ‘3-dimensionality’ through late-stage functionalization of extended (hetero)aromatic systems is a powerful synthetic approach. The abundance of starting materials and cross-coupling methodologies to access the precursors allows for highly diverse products. Subsequent selective partial reduction can alter the core structure in a manner of interest to medicinal chemists. Herein, we describe the precise, partial reduction of multicyclic heteroaromatic systems using a simple heterogeneous catalyst. The approach can be extended to introduce deuterium (again at late-stage). Excellent yields can be obtained using simple reaction conditions.

Keywords

Pharmaceutical drug design , Medicinal chemists. , (Hetero)aromatic systems , Molecular editing , 3-dimensionality , AcOD-d4 , Deuterium

Citation

Kehoe, R.A., Lowry, A., Light, M.E., Jones, D.J., Byrne, P.A. and McGlacken, G.P. (2024) ‘Regioselective partial hydrogenation and deuteration of tetracyclic (Hetero)aromatic systems using a simple heterogeneous catalyst’, Chemistry – A European Journal, e202400102 (7 pp). Available at: https://doi.org/10.1002/chem.202400102.