Recyclable N-heterocyclic carbene/palladium catalyst on graphene oxide for the aqueous-phase Suzuki reaction

Jung Hyun Park; Faizan Raza; Su Ji Jeon; Hye In Kim; Tae Woog Kang; Dabin Yim; Jong Ho Kim

doi:10.1016/j.tetlet.2014.04.078

Recyclable N-heterocyclic carbene/palladium catalyst on graphene oxide for the aqueous-phase Suzuki reaction

Jung Hyun Park, Faizan Raza, Su Ji Jeon, Hye In Kim, Tae Woog Kang, Dabin Yim, Jong Ho Kim

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

Abstract

Graphene oxide (GO) was functionalized with a N-heterocyclic carbene (NHC) precursor, 3-(3-aminopropyl)-1-methylimidazolium bromide ([APMIm][Br]) for the immobilization of palladium catalyst. The GO-supported NHC precursor (IMGO) formed a stable complex with Pd(OAc)₂ (GO-NHC-Pd), which showed excellent catalytic activity and fast reaction kinetics in the aqueous-phase Suzuki reaction of aryl bromides and chlorides at relatively mild conditions (1 h at 50 °C). The GO-NHC-Pd catalyst was reused several times without any loss of its catalytic activity in the Suzuki reaction of aryl bromide.

Original language	English (US)
Pages (from-to)	3426-3430
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2014.04.078
State	Published - Jun 4 2014
Externally published	Yes

Keywords

Graphene oxide (GO)
Heterogeneous catalyst
N-Heterocyclic carbene (NHC)
Palladium catalyst
Suzuki reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Online availability

10.1016/j.tetlet.2014.04.078

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@article{53df5fd13dbc443a90ccd0d77f57df36,

title = "Recyclable N-heterocyclic carbene/palladium catalyst on graphene oxide for the aqueous-phase Suzuki reaction",

abstract = "Graphene oxide (GO) was functionalized with a N-heterocyclic carbene (NHC) precursor, 3-(3-aminopropyl)-1-methylimidazolium bromide ([APMIm][Br]) for the immobilization of palladium catalyst. The GO-supported NHC precursor (IMGO) formed a stable complex with Pd(OAc)2 (GO-NHC-Pd), which showed excellent catalytic activity and fast reaction kinetics in the aqueous-phase Suzuki reaction of aryl bromides and chlorides at relatively mild conditions (1 h at 50 °C). The GO-NHC-Pd catalyst was reused several times without any loss of its catalytic activity in the Suzuki reaction of aryl bromide.",

keywords = "Graphene oxide (GO), Heterogeneous catalyst, N-Heterocyclic carbene (NHC), Palladium catalyst, Suzuki reaction",

author = "Park, {Jung Hyun} and Faizan Raza and Jeon, {Su Ji} and Kim, {Hye In} and Kang, {Tae Woog} and Dabin Yim and Kim, {Jong Ho}",

note = "Funding Information: This work was supported by the research fund of Hanyang University ( HY-2011-N ). ",

year = "2014",

month = jun,

day = "4",

doi = "10.1016/j.tetlet.2014.04.078",

language = "English (US)",

volume = "55",

pages = "3426--3430",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "23",

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TY - JOUR

T1 - Recyclable N-heterocyclic carbene/palladium catalyst on graphene oxide for the aqueous-phase Suzuki reaction

AU - Park, Jung Hyun

AU - Raza, Faizan

AU - Jeon, Su Ji

AU - Kim, Hye In

AU - Kang, Tae Woog

AU - Yim, Dabin

AU - Kim, Jong Ho

N1 - Funding Information: This work was supported by the research fund of Hanyang University ( HY-2011-N ).

PY - 2014/6/4

Y1 - 2014/6/4

N2 - Graphene oxide (GO) was functionalized with a N-heterocyclic carbene (NHC) precursor, 3-(3-aminopropyl)-1-methylimidazolium bromide ([APMIm][Br]) for the immobilization of palladium catalyst. The GO-supported NHC precursor (IMGO) formed a stable complex with Pd(OAc)2 (GO-NHC-Pd), which showed excellent catalytic activity and fast reaction kinetics in the aqueous-phase Suzuki reaction of aryl bromides and chlorides at relatively mild conditions (1 h at 50 °C). The GO-NHC-Pd catalyst was reused several times without any loss of its catalytic activity in the Suzuki reaction of aryl bromide.

AB - Graphene oxide (GO) was functionalized with a N-heterocyclic carbene (NHC) precursor, 3-(3-aminopropyl)-1-methylimidazolium bromide ([APMIm][Br]) for the immobilization of palladium catalyst. The GO-supported NHC precursor (IMGO) formed a stable complex with Pd(OAc)2 (GO-NHC-Pd), which showed excellent catalytic activity and fast reaction kinetics in the aqueous-phase Suzuki reaction of aryl bromides and chlorides at relatively mild conditions (1 h at 50 °C). The GO-NHC-Pd catalyst was reused several times without any loss of its catalytic activity in the Suzuki reaction of aryl bromide.

KW - Graphene oxide (GO)

KW - Heterogeneous catalyst

KW - N-Heterocyclic carbene (NHC)

KW - Palladium catalyst

KW - Suzuki reaction

UR - http://www.scopus.com/inward/record.url?scp=84901494773&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84901494773&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.04.078

DO - 10.1016/j.tetlet.2014.04.078

M3 - Article

AN - SCOPUS:84901494773

SN - 0040-4039

VL - 55

SP - 3426

EP - 3430

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Recyclable N-heterocyclic carbene/palladium catalyst on graphene oxide for the aqueous-phase Suzuki reaction

Abstract

Keywords

ASJC Scopus subject areas

Online availability

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