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Issue 10, 2013
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Development of a 4,4′-biphenyl/phosphine-based COF for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene

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Abstract

The improved synthesis, characterisation and application of a microporous 4,4′-biphenyl/phosphine-based covalent organic framework (COF) for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene with phenol and glycerol are presented. The solid polyphosphine is amorphous, microporous and an excellent support for Pd(acac)2. Solid-state NMR and DRIFT analysis of materials of varying Pd-loading show that bis-phosphine complexes of palladium are preferably formed. Under solvent- and base-free conditions, high conversions and selectivities are obtained for this catalyst material with both phenol and glycerol as substrates. The product selectivity, with both butenylation and telomerisation activity observed with phenol, can be tuned by variation of the metal loading. For glycerol it is shown that the selectivity to the undesired tri telomer is low under all applied conditions and, remarkably, that the heterogeneous catalyst outperforms its homogeneous PPh3-based counterpart.

Graphical abstract: Development of a 4,4′-biphenyl/phosphine-based COF for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene

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Article information


Submitted
21 Mar 2013
Accepted
02 Jul 2013
First published
30 Jul 2013

Catal. Sci. Technol., 2013,3, 2571-2579
Article type
Paper

Development of a 4,4′-biphenyl/phosphine-based COF for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene

P. J. C. Hausoul, T. M. Eggenhuisen, D. Nand, M. Baldus, B. M. Weckhuysen, R. J. M. Klein Gebbink and P. C. A. Bruijnincx, Catal. Sci. Technol., 2013, 3, 2571
DOI: 10.1039/C3CY00188A

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