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

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posted on 2024-05-29, 14:14 authored by Roberta A. Kehoe, Amy Lowry, Mark E. Light, David J. Jones, Peter A. Byrne, Gerard P. McGlacken

The introduction of added ‘3-dimensionality’ through late-stage functionalisation 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.

Funding

The Direct Arylation of Pyrones, Coumarins, Pyridones and Quinolones

Science Foundation Ireland

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Synthesis and Solid State Pharmaceutical Centre (SSPC)

Science Foundation Ireland

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SSPC_Phase 2

Science Foundation Ireland

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SOSEarth: Sustainable Organic Synthesis using Earth Abundant Metals for Critical Pharmaceutical Transformations

Science Foundation Ireland

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History

Publication

Chemistry, 2024, 30, e202400102

Publisher

Wiley and Sons Ltd.,

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  • Synthesis and Solid State Pharmaceutical Centre

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