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

Roberto Ricciardi; Jurriaan Huskens; Willem Verboom

doi:10.1039/C5OB00289C

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

Roberto Ricciardi, Jurriaan Huskens, Willem Verboom^*

^*Corresponding author for this work

Molecular Nanofabrication

Research output: Contribution to journal › Article › Academic › peer-review

20 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4953-4959
Number of pages	7
Journal	Organic & biomolecular chemistry
Volume	13
Issue number	17
DOIs	https://doi.org/10.1039/C5OB00289C
Publication status	Published - 7 May 2015

Keywords

2023 OA procedure

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10.1039/C5OB00289C

ArticleFinal published version, 485 KBLicence: Taverne
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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.",

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AB - 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.

KW - 2023 OA procedure

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DO - 10.1039/C5OB00289C

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

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