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

Research output: Contribution to journalArticleAcademicpeer-review

16 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 languageUndefined
Pages (from-to)4953-4959
Number of pages7
JournalOrganic & biomolecular chemistry
Volume13
DOIs
Publication statusPublished - 2015

Keywords

  • IR-99885
  • METIS-314636

Cite this

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title = "Dendrimer-encapsulated Pd nanoparticles as catalysts for C-C cross-couplings in flow microreactors",
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.",
keywords = "IR-99885, METIS-314636",
author = "R. Ricciardi and Jurriaan Huskens and Willem Verboom",
year = "2015",
doi = "10.1039/C5OB00289C",
language = "Undefined",
volume = "13",
pages = "4953--4959",
journal = "Organic & biomolecular chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",

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Dendrimer-encapsulated Pd nanoparticles as catalysts for C-C cross-couplings in flow microreactors. / Ricciardi, R.; Huskens, Jurriaan; Verboom, Willem.

In: Organic & biomolecular chemistry, Vol. 13, 2015, p. 4953-4959.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Dendrimer-encapsulated Pd nanoparticles as catalysts for C-C cross-couplings in flow microreactors

AU - Ricciardi, R.

AU - Huskens, Jurriaan

AU - Verboom, Willem

PY - 2015

Y1 - 2015

N2 - 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.

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 - IR-99885

KW - METIS-314636

U2 - 10.1039/C5OB00289C

DO - 10.1039/C5OB00289C

M3 - Article

VL - 13

SP - 4953

EP - 4959

JO - Organic & biomolecular chemistry

JF - Organic & biomolecular chemistry

SN - 1477-0520

ER -