A direct pathway for the coupling of arenes and alkylamines via a heterogeneous zeolite-based photocatalyst

Vincent Lemmens; Kwinten Janssens; Jorge Gascon; Dirk E. De Vos

doi:10.1039/d3gc01225e

A direct pathway for the coupling of arenes and alkylamines via a heterogeneous zeolite-based photocatalyst

Vincent Lemmens, Kwinten Janssens, Jorge Gascon, Dirk E. De Vos

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Abstract

The production of N,N-dialkyl arylamines is relevant for a range of high-value materials such as pharmaceuticals, agrochemicals and organic materials. In general, these molecules are assembled via multiple pre-functionalization steps of the aromatic compound and a subsequent cross-coupling with the arylamine under harsh conditions. In this manuscript, we develop a more sustainable and efficient method for the direct C–H amination of arenes and alkylamines using Ru(bipy)32+ entrapped in the supercages of a faujasite support (CBV-100). This creates a heterogeneous photocatalyst that can be used under visible light irradiation. Furthermore, the mesomeric and/or inductive effects of the substituent groups on the arene coupling partner are thoroughly investigated using Hammett plots, leading to a rationally guided solvent selection (HFIP or CH3CN). Using reduced reaction temperatures (

Original language	English (US)
Journal	Green Chemistry
DOIs	https://doi.org/10.1039/d3gc01225e
State	Published - Jun 14 2023

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Environmental Chemistry
Pollution

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title = "A direct pathway for the coupling of arenes and alkylamines via a heterogeneous zeolite-based photocatalyst",

abstract = "The production of N,N-dialkyl arylamines is relevant for a range of high-value materials such as pharmaceuticals, agrochemicals and organic materials. In general, these molecules are assembled via multiple pre-functionalization steps of the aromatic compound and a subsequent cross-coupling with the arylamine under harsh conditions. In this manuscript, we develop a more sustainable and efficient method for the direct C–H amination of arenes and alkylamines using Ru(bipy)32+ entrapped in the supercages of a faujasite support (CBV-100). This creates a heterogeneous photocatalyst that can be used under visible light irradiation. Furthermore, the mesomeric and/or inductive effects of the substituent groups on the arene coupling partner are thoroughly investigated using Hammett plots, leading to a rationally guided solvent selection (HFIP or CH3CN). Using reduced reaction temperatures (",

author = "Vincent Lemmens and Kwinten Janssens and Jorge Gascon and {De Vos}, {Dirk E.}",

note = "KAUST Repository Item: Exported on 2023-07-04 Acknowledged KAUST grant number(s): OSR-2018-CRG7-3741.2 Acknowledgements: The research leading to these results has received funding from the KAUST-CRG Program (OSR-2018-CRG7-3741.2). K. J. and D. E. D. V. thank FWO for project funding (grant no. G0F2320N). We acknowledge the SUPERXAS beamline at Swiss Light sourc (SLS, Switzerland) for providing the beamtime and Dr. Aram Bugaev for the professional support during the measurements. V. L. is thanking Carlos Marquez for the ICP-OES measurements.",

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doi = "10.1039/d3gc01225e",

language = "English (US)",

journal = "Green Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - A direct pathway for the coupling of arenes and alkylamines via a heterogeneous zeolite-based photocatalyst

AU - Lemmens, Vincent

AU - Janssens, Kwinten

AU - Gascon, Jorge

AU - De Vos, Dirk E.

N1 - KAUST Repository Item: Exported on 2023-07-04 Acknowledged KAUST grant number(s): OSR-2018-CRG7-3741.2 Acknowledgements: The research leading to these results has received funding from the KAUST-CRG Program (OSR-2018-CRG7-3741.2). K. J. and D. E. D. V. thank FWO for project funding (grant no. G0F2320N). We acknowledge the SUPERXAS beamline at Swiss Light sourc (SLS, Switzerland) for providing the beamtime and Dr. Aram Bugaev for the professional support during the measurements. V. L. is thanking Carlos Marquez for the ICP-OES measurements.

PY - 2023/6/14

Y1 - 2023/6/14

N2 - The production of N,N-dialkyl arylamines is relevant for a range of high-value materials such as pharmaceuticals, agrochemicals and organic materials. In general, these molecules are assembled via multiple pre-functionalization steps of the aromatic compound and a subsequent cross-coupling with the arylamine under harsh conditions. In this manuscript, we develop a more sustainable and efficient method for the direct C–H amination of arenes and alkylamines using Ru(bipy)32+ entrapped in the supercages of a faujasite support (CBV-100). This creates a heterogeneous photocatalyst that can be used under visible light irradiation. Furthermore, the mesomeric and/or inductive effects of the substituent groups on the arene coupling partner are thoroughly investigated using Hammett plots, leading to a rationally guided solvent selection (HFIP or CH3CN). Using reduced reaction temperatures (

AB - The production of N,N-dialkyl arylamines is relevant for a range of high-value materials such as pharmaceuticals, agrochemicals and organic materials. In general, these molecules are assembled via multiple pre-functionalization steps of the aromatic compound and a subsequent cross-coupling with the arylamine under harsh conditions. In this manuscript, we develop a more sustainable and efficient method for the direct C–H amination of arenes and alkylamines using Ru(bipy)32+ entrapped in the supercages of a faujasite support (CBV-100). This creates a heterogeneous photocatalyst that can be used under visible light irradiation. Furthermore, the mesomeric and/or inductive effects of the substituent groups on the arene coupling partner are thoroughly investigated using Hammett plots, leading to a rationally guided solvent selection (HFIP or CH3CN). Using reduced reaction temperatures (

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UR - http://xlink.rsc.org/?DOI=D3GC01225E

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DO - 10.1039/d3gc01225e

M3 - Article

SN - 1463-9270

JO - Green Chemistry

JF - Green Chemistry

ER -

A direct pathway for the coupling of arenes and alkylamines via a heterogeneous zeolite-based photocatalyst

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