Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media.

Jason E. Camp; Jay J. Dunsford; Oliver S. G. Dacosta; Rebecca K. Blundell; James Adams; Joshua Britton; Robert J. Smith; Thomas W. Bousfield; Michael W. Fay

doi:10.1039/C5RA25712C

Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media.

Jason E. Camp, Jay J. Dunsford, Oliver S. G. Dacosta, Rebecca K. Blundell, James Adams, Joshua Britton, Robert J. Smith, Thomas W. Bousfield, Michael W. Fay

Department of Chemistry

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

20 Citations (SciVal)

Abstract

In situ-generated, glucose-derived palladium(0) nanoparticles were shown to be convenient and effective catalysts for aq. Mizoroki-Heck, Sonogashira and Suzuki-Miyaura cross-coupling reactions. The addn. of only 4-10 mol% glucose to the reaction mixt. lead to a significant increase in yield of the desired products in comparison to processes that omitted the renewable sugar. The Mizoroki-Heck reaction was obsd. to proceed in good yield even as the reaction reached acidic pH levels. Extensive anal. of the size and morphol. of the in situ-formed palladium nanoparticles using advanced anal. techniques showed that the zero valent metal was surrounded by hydrophilic hydroxyl groups. The increased aq. phase affinity afforded by these groups allowed for facile recycling of the catalyst. [on SciFinder(R)]

Original language	English
Pages (from-to)	16115-16121
Number of pages	7
Journal	RSC Advances
Volume	6
Issue number	20
Early online date	8 Feb 2016
DOIs	https://doi.org/10.1039/C5RA25712C
Publication status	Published - 2016

Bibliographical note

M1 - Copyright (C) 2018 American Chemical Society (ACS). All Rights Reserved.

CAPLUS AN 2016:213322(Journal; Online Computer File)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

biaryl prepn green
dialkyl acetylene prepn green
styrene prepn green diastereoselective
aryl iodide alkene Mizoroki Heck coupling glucose palladium nanocatalyst
phenyl acetylene aryl iodide Sonogashira coupling glucose palladium nanocatalyst
boronic acid aryl iodide Suzuki coupling glucose palladium nanocatalyst

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10.1039/C5RA25712C

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title = "Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media.",

abstract = "In situ-generated, glucose-derived palladium(0) nanoparticles were shown to be convenient and effective catalysts for aq. Mizoroki-Heck, Sonogashira and Suzuki-Miyaura cross-coupling reactions. The addn. of only 4-10 mol\% glucose to the reaction mixt. lead to a significant increase in yield of the desired products in comparison to processes that omitted the renewable sugar. The Mizoroki-Heck reaction was obsd. to proceed in good yield even as the reaction reached acidic pH levels. Extensive anal. of the size and morphol. of the in situ-formed palladium nanoparticles using advanced anal. techniques showed that the zero valent metal was surrounded by hydrophilic hydroxyl groups. The increased aq. phase affinity afforded by these groups allowed for facile recycling of the catalyst. [on SciFinder(R)]",

keywords = "biaryl prepn green, dialkyl acetylene prepn green, styrene prepn green diastereoselective, aryl iodide alkene Mizoroki Heck coupling glucose palladium nanocatalyst, phenyl acetylene aryl iodide Sonogashira coupling glucose palladium nanocatalyst, boronic acid aryl iodide Suzuki coupling glucose palladium nanocatalyst",

author = "Camp, \{Jason E.\} and Dunsford, \{Jay J.\} and Dacosta, \{Oliver S. G.\} and Blundell, \{Rebecca K.\} and James Adams and Joshua Britton and Smith, \{Robert J.\} and Bousfield, \{Thomas W.\} and Fay, \{Michael W.\}",

year = "2016",

doi = "10.1039/C5RA25712C",

language = "English",

volume = "6",

pages = "16115--16121",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "20",

}

TY - JOUR

T1 - Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media.

AU - Camp, Jason E.

AU - Dunsford, Jay J.

AU - Dacosta, Oliver S. G.

AU - Blundell, Rebecca K.

AU - Adams, James

AU - Britton, Joshua

AU - Smith, Robert J.

AU - Bousfield, Thomas W.

AU - Fay, Michael W.

PY - 2016

Y1 - 2016

N2 - In situ-generated, glucose-derived palladium(0) nanoparticles were shown to be convenient and effective catalysts for aq. Mizoroki-Heck, Sonogashira and Suzuki-Miyaura cross-coupling reactions. The addn. of only 4-10 mol% glucose to the reaction mixt. lead to a significant increase in yield of the desired products in comparison to processes that omitted the renewable sugar. The Mizoroki-Heck reaction was obsd. to proceed in good yield even as the reaction reached acidic pH levels. Extensive anal. of the size and morphol. of the in situ-formed palladium nanoparticles using advanced anal. techniques showed that the zero valent metal was surrounded by hydrophilic hydroxyl groups. The increased aq. phase affinity afforded by these groups allowed for facile recycling of the catalyst. [on SciFinder(R)]

AB - In situ-generated, glucose-derived palladium(0) nanoparticles were shown to be convenient and effective catalysts for aq. Mizoroki-Heck, Sonogashira and Suzuki-Miyaura cross-coupling reactions. The addn. of only 4-10 mol% glucose to the reaction mixt. lead to a significant increase in yield of the desired products in comparison to processes that omitted the renewable sugar. The Mizoroki-Heck reaction was obsd. to proceed in good yield even as the reaction reached acidic pH levels. Extensive anal. of the size and morphol. of the in situ-formed palladium nanoparticles using advanced anal. techniques showed that the zero valent metal was surrounded by hydrophilic hydroxyl groups. The increased aq. phase affinity afforded by these groups allowed for facile recycling of the catalyst. [on SciFinder(R)]

KW - biaryl prepn green

KW - dialkyl acetylene prepn green

KW - styrene prepn green diastereoselective

KW - aryl iodide alkene Mizoroki Heck coupling glucose palladium nanocatalyst

KW - phenyl acetylene aryl iodide Sonogashira coupling glucose palladium nanocatalyst

KW - boronic acid aryl iodide Suzuki coupling glucose palladium nanocatalyst

UR - https://www.scopus.com/pages/publications/84958092589

U2 - 10.1039/C5RA25712C

DO - 10.1039/C5RA25712C

M3 - Article

SN - 2046-2069

VL - 6

SP - 16115

EP - 16121

JO - RSC Advances

JF - RSC Advances

IS - 20

ER -

Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media.

Abstract

Bibliographical note

UN SDGs

Keywords

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