Issue 13, 2023

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 (<0 °C) drastically improves the product yield, while suppressing the generation of side products.

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

Supplementary files

Article information

Article type
Paper
Submitted
14 4 2023
Accepted
07 6 2023
First published
14 6 2023

Green Chem., 2023,25, 5113-5122

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

V. Lemmens, K. Janssens, J. Gascon and D. E. De Vos, Green Chem., 2023, 25, 5113 DOI: 10.1039/D3GC01225E

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