Amphiphilic ionic palladium complexes for aqueous-organic biphasic Sonogashira reactions under aerobic and CuI-free conditions

Xuezhu Wang; Jing Zhang; Yongyong Wang; Ye Liu

doi:10.1016/j.catcom.2013.05.005

Amphiphilic ionic palladium complexes for aqueous-organic biphasic Sonogashira reactions under aerobic and CuI-free conditions

Xuezhu Wang
, Jing Zhang
, Yongyong Wang
, Ye Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

10 Scopus citations

Abstract

The ionic Pd(II)-complexes of 2 (ammonium-[1-(2-hydroxyethyl)-3- methylimidazolium] bis[3-(diphenylphosphino)benzenesulfonate]- dichloropalladium(II) ([(NH₄)(Hemim)][PdCl₂(TPPMS) ₂])) and 3 (bis[1-n-butyl-3-methylimidazolium] bis[3- (diphenylphosphino)benzenesulfonate]-dichloropalladium(II) ([Bmim] ₂[PdCl₂(TPPMS)₂])) were synthesized and fully characterized. The single crystal X-ray diffraction analyses show that 2 and 3 are composed of the imidazolium-based cations and [PdCl₂(TPPMS) ₂]^{2 -} anions. The properties of such imidazolium-based Pd-complexes of 2 and 3, in terms of the aqueous solubilities and the catalytic behaviors in water, could be dramatically varied. When 2 and 3 were applied as the precatalysts for the Sonogashira coupling of iodobenzene with phenylacetylene under aerobic and CuI-free conditions, the much higher yields of 1,2-diphenylethyne were obtained due to their amphiphilicity. The wide generality of 2 was available for aqueous-organic biphasic Sonogashira reactions.

Original language	English
Pages (from-to)	23-26
Number of pages	4
Journal	Catalysis Communications
Volume	40
DOIs	https://doi.org/10.1016/j.catcom.2013.05.005
State	Published - 2013

Keywords

Biphasic catalysis
Ionic complexes
Sonogashira reaction
Water-soluble palladium complexes

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10.1016/j.catcom.2013.05.005

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@article{b421a1fad5224c8ab4f398480a6d4d01,

title = "Amphiphilic ionic palladium complexes for aqueous-organic biphasic Sonogashira reactions under aerobic and CuI-free conditions",

abstract = "The ionic Pd(II)-complexes of 2 (ammonium-[1-(2-hydroxyethyl)-3- methylimidazolium] bis[3-(diphenylphosphino)benzenesulfonate]- dichloropalladium(II) ([(NH4)(Hemim)][PdCl2(TPPMS) 2])) and 3 (bis[1-n-butyl-3-methylimidazolium] bis[3- (diphenylphosphino)benzenesulfonate]-dichloropalladium(II) ([Bmim] 2[PdCl2(TPPMS)2])) were synthesized and fully characterized. The single crystal X-ray diffraction analyses show that 2 and 3 are composed of the imidazolium-based cations and [PdCl2(TPPMS) 2]2 - anions. The properties of such imidazolium-based Pd-complexes of 2 and 3, in terms of the aqueous solubilities and the catalytic behaviors in water, could be dramatically varied. When 2 and 3 were applied as the precatalysts for the Sonogashira coupling of iodobenzene with phenylacetylene under aerobic and CuI-free conditions, the much higher yields of 1,2-diphenylethyne were obtained due to their amphiphilicity. The wide generality of 2 was available for aqueous-organic biphasic Sonogashira reactions.",

keywords = "Biphasic catalysis, Ionic complexes, Sonogashira reaction, Water-soluble palladium complexes",

author = "Xuezhu Wang and Jing Zhang and Yongyong Wang and Ye Liu",

year = "2013",

doi = "10.1016/j.catcom.2013.05.005",

language = "英语",

volume = "40",

pages = "23--26",

journal = "Catalysis Communications",

issn = "1566-7367",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Amphiphilic ionic palladium complexes for aqueous-organic biphasic Sonogashira reactions under aerobic and CuI-free conditions

AU - Wang, Xuezhu

AU - Zhang, Jing

AU - Wang, Yongyong

AU - Liu, Ye

PY - 2013

Y1 - 2013

N2 - The ionic Pd(II)-complexes of 2 (ammonium-[1-(2-hydroxyethyl)-3- methylimidazolium] bis[3-(diphenylphosphino)benzenesulfonate]- dichloropalladium(II) ([(NH4)(Hemim)][PdCl2(TPPMS) 2])) and 3 (bis[1-n-butyl-3-methylimidazolium] bis[3- (diphenylphosphino)benzenesulfonate]-dichloropalladium(II) ([Bmim] 2[PdCl2(TPPMS)2])) were synthesized and fully characterized. The single crystal X-ray diffraction analyses show that 2 and 3 are composed of the imidazolium-based cations and [PdCl2(TPPMS) 2]2 - anions. The properties of such imidazolium-based Pd-complexes of 2 and 3, in terms of the aqueous solubilities and the catalytic behaviors in water, could be dramatically varied. When 2 and 3 were applied as the precatalysts for the Sonogashira coupling of iodobenzene with phenylacetylene under aerobic and CuI-free conditions, the much higher yields of 1,2-diphenylethyne were obtained due to their amphiphilicity. The wide generality of 2 was available for aqueous-organic biphasic Sonogashira reactions.

AB - The ionic Pd(II)-complexes of 2 (ammonium-[1-(2-hydroxyethyl)-3- methylimidazolium] bis[3-(diphenylphosphino)benzenesulfonate]- dichloropalladium(II) ([(NH4)(Hemim)][PdCl2(TPPMS) 2])) and 3 (bis[1-n-butyl-3-methylimidazolium] bis[3- (diphenylphosphino)benzenesulfonate]-dichloropalladium(II) ([Bmim] 2[PdCl2(TPPMS)2])) were synthesized and fully characterized. The single crystal X-ray diffraction analyses show that 2 and 3 are composed of the imidazolium-based cations and [PdCl2(TPPMS) 2]2 - anions. The properties of such imidazolium-based Pd-complexes of 2 and 3, in terms of the aqueous solubilities and the catalytic behaviors in water, could be dramatically varied. When 2 and 3 were applied as the precatalysts for the Sonogashira coupling of iodobenzene with phenylacetylene under aerobic and CuI-free conditions, the much higher yields of 1,2-diphenylethyne were obtained due to their amphiphilicity. The wide generality of 2 was available for aqueous-organic biphasic Sonogashira reactions.

KW - Biphasic catalysis

KW - Ionic complexes

KW - Sonogashira reaction

KW - Water-soluble palladium complexes

UR - https://www.scopus.com/pages/publications/84879334795

U2 - 10.1016/j.catcom.2013.05.005

DO - 10.1016/j.catcom.2013.05.005

M3 - 文章

AN - SCOPUS:84879334795

SN - 1566-7367

VL - 40

SP - 23

EP - 26

JO - Catalysis Communications

JF - Catalysis Communications

ER -

Amphiphilic ionic palladium complexes for aqueous-organic biphasic Sonogashira reactions under aerobic and CuI-free conditions

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Keywords

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