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

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

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.

Dearomatisation, deuteration, heterocycle, hydrogenation, regioselective, simple catalyst
0947-6539
Kehoe, Roberta A.
fe06d727-db10-420d-a03a-a4e26042010e
Lowry, Amy
61571a3b-4160-4225-817e-3be5a61370e5
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Jones, David J.
7985500f-79fb-43c0-8d19-b563062c0aeb
Byrne, Peter
9b34717d-0af6-40d7-a9b2-08e0be3dabb4
McGlacken, Gerard P.
7232768a-94ff-4794-81b3-1467726505e0
Kehoe, Roberta A.
fe06d727-db10-420d-a03a-a4e26042010e
Lowry, Amy
61571a3b-4160-4225-817e-3be5a61370e5
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Jones, David J.
7985500f-79fb-43c0-8d19-b563062c0aeb
Byrne, Peter
9b34717d-0af6-40d7-a9b2-08e0be3dabb4
McGlacken, Gerard P.
7232768a-94ff-4794-81b3-1467726505e0

Kehoe, Roberta A., Lowry, Amy, Light, Mark E., Jones, David J., Byrne, Peter and McGlacken, Gerard P. (2024) Regioselective partial hydrogenation and deuteration of tetracyclic (hetero)aromatic systems using a simple heterogeneous catalyst. Chemistry - A European Journal, 30 (17), [e202400102]. (doi:10.1002/chem.202400102).

Record type: Article

Abstract

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.

Text
Chemistry A European J - 2024 - Kehoe - Regioselective Partial Hydrogenation and Deuteration of Tetracyclic Hetero - Accepted Manuscript
Available under License Creative Commons Attribution.
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More information

Accepted/In Press date: 12 January 2024
e-pub ahead of print date: 12 January 2024
Published date: 20 March 2024
Additional Information: Publisher Copyright: © 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Keywords: Dearomatisation, deuteration, heterocycle, hydrogenation, regioselective, simple catalyst

Identifiers

Local EPrints ID: 486631
URI: http://eprints.soton.ac.uk/id/eprint/486631
ISSN: 0947-6539
PURE UUID: 0ccf6e4f-1992-419a-bef0-491608422df3
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 29 Jan 2024 17:32
Last modified: 16 Apr 2024 01:36

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Contributors

Author: Roberta A. Kehoe
Author: Amy Lowry
Author: Mark E. Light ORCID iD
Author: David J. Jones
Author: Peter Byrne
Author: Gerard P. McGlacken

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