Regioselective Partial Hydrogenation and Deuteration of Tetracyclic (Hetero)aromatic Systems Using a Simple Heterogeneous Catalyst

Author:

Kehoe Roberta A.12,Lowry Amy1,Light Mark E.3,Jones David J.4,Byrne Peter A.25,McGlacken Gerard P.12ORCID

Affiliation:

1. School of Chemistry Analytical and Biological Chemistry Research Facility University College Cork, Robert Kane Building Western Road Cork

2. Synthesis and Solid State Pharmaceutical Centre (SSPC) University of Limerick Limerick

3. Department of Chemistry University of Southampton SO17 1BJ United Kingdom

4. EaStCHEM School of Chemistry University of Edinburgh, Joseph-Black Building David Brewster Road Edinburgh EH9 3FJ United Kingdom

5. Centre for Synthesis and Chemical Biology School of Chemistry University College Dublin Belfield Dublin 4 Ireland

Abstract

AbstractThe 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.

Funder

Science Foundation Ireland

Publisher

Wiley

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