Access to electron-rich dibenzofurans through NBu4OAc-mediated palladium catalysis
Access to electron-rich dibenzofurans through NBu4OAc-mediated palladium catalysis
Dibenzofuran and its derivatives are ubiquitous and important medicinal and natural products. Many contain electron-rich aryl rings. Forming the key intramolecular Ar−Ar bond using traditional cross-coupling is difficult. The C−H functionalisation (C−H activation) approach is, in principle, far more useful. However, we previously found that the well-established conditions, which promote C−H functionalisation through Concerted Metalation-Deprotonation (CMD), proved unsatisfactory. Herein, we report a Pd-catalysed C−H functionalisation protocol that works with electron-rich arenes. We use tetrabutylammonium acetate (NBu4OAc), which we suspect can act as base, ligand and solvent, rendering this protocol a simple and efficient route to electron-rich dibenzofurans.
catalysis, tetraalkylammonium salt, Dibenzofuran, electron-rich, palladium
Power, Mark
d1f873dd-2dbc-4896-a516-6e818cbd7795
Mackey, Katrina
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Light, Mark E.
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Jones, David J.
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McGlacken, Gerard P.
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21 November 2023
Power, Mark
d1f873dd-2dbc-4896-a516-6e818cbd7795
Mackey, Katrina
20b2d718-5873-48c3-9782-d752e9cc7092
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Jones, David J.
f8d7ade5-9012-46ea-818d-ed61937298dc
McGlacken, Gerard P.
7232768a-94ff-4794-81b3-1467726505e0
Power, Mark, Mackey, Katrina, Light, Mark E., Jones, David J. and McGlacken, Gerard P.
(2023)
Access to electron-rich dibenzofurans through NBu4OAc-mediated palladium catalysis.
European Journal of Organic Chemistry, 26 (44), [e202300790].
(doi:10.1002/ejoc.202300790).
Abstract
Dibenzofuran and its derivatives are ubiquitous and important medicinal and natural products. Many contain electron-rich aryl rings. Forming the key intramolecular Ar−Ar bond using traditional cross-coupling is difficult. The C−H functionalisation (C−H activation) approach is, in principle, far more useful. However, we previously found that the well-established conditions, which promote C−H functionalisation through Concerted Metalation-Deprotonation (CMD), proved unsatisfactory. Herein, we report a Pd-catalysed C−H functionalisation protocol that works with electron-rich arenes. We use tetrabutylammonium acetate (NBu4OAc), which we suspect can act as base, ligand and solvent, rendering this protocol a simple and efficient route to electron-rich dibenzofurans.
Text
Eur J Org Chem - 2023 - Power - Access to Electron‐Rich Dibenzofurans through NBu4OAc‐Mediated Palladium Catalysis
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e-pub ahead of print date: 13 September 2023
Published date: 21 November 2023
Additional Information:
Funding Information:
This research was supported by the Irish Research Council (GOIPG/2019/952) and Science Foundation Ireland, through the Research Frontiers Programme (21/FFP‐A/8784) and the Synthesis and Solid State Pharmaceutical Centre (SSPC) (SFI/12/RC/2275 and SFI/ 846 12/RC2275_P2). Open Access funding provided by IReL.
Keywords:
catalysis, tetraalkylammonium salt, Dibenzofuran, electron-rich, palladium
Identifiers
Local EPrints ID: 483751
URI: http://eprints.soton.ac.uk/id/eprint/483751
ISSN: 1434-193X
PURE UUID: 54b98461-b04f-421e-b9f4-44066b6e8c3a
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Date deposited: 03 Nov 2023 18:11
Last modified: 18 Mar 2024 02:50
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Contributors
Author:
Mark Power
Author:
Katrina Mackey
Author:
David J. Jones
Author:
Gerard P. McGlacken
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