Issue 17, 2015
From the journal:

Organic & Biomolecular Chemistry

Dendrimer-encapsulated Pd nanoparticles as catalysts for C–C cross-couplings in flow microreactors†

Roberto Ricciardi,a   Jurriaan Huskensa  and  Willem Verboom*a  

* Corresponding authors

a Laboratory of Molecular Nanofabrication, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands
E-mail: w.verboom@utwente.nl

Abstract

The inner walls of glass microreactors were functionalized with dendrimer-encapsulated Pd nanoparticles. The catalysts were efficient for the Heck–Cassar (copper-free Sonogashira) and Suzuki–Miyaura (SMC) cross-coupling reactions. For the Heck–Cassar reaction between iodobenzene and phenylacetylene, the catalytic system exhibited a high turnover frequency (TOF) and on average required milder reaction conditions as compared to other continuous flow cross-couplings. A study of the substituent effect of para-substituted aryl halides revealed a beneficial effect of electron-withdrawing side groups for the SMC. Moreover, a reaction constant (ρ) of 1.5, determined from the Hammett plot, indicated a possible rate-determining step other than the oxidative addition.

Graphical abstract: Dendrimer-encapsulated Pd nanoparticles as catalysts for C–C cross-couplings in flow microreactors

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Article information

DOI
https://doi.org/10.1039/C5OB00289C
Article type
Paper
Submitted
10 Feb 2015
Accepted
18 Mar 2015
First published
18 Mar 2015

Org. Biomol. Chem., 2015,13, 4953-4959

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Dendrimer-encapsulated Pd nanoparticles as catalysts for C–C cross-couplings in flow microreactors

R. Ricciardi, J. Huskens and W. Verboom, Org. Biomol. Chem., 2015, 13, 4953 DOI: 10.1039/C5OB00289C

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