Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

Paul Raithby; Mojtaba Bagherzadeh; Hamed Mahmoudi; Saeed Ataie; Mohammad Bahjati; Reza Kia; Luigi Vaccaro

doi:10.1016/j.mcat.2019.110406

Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

Paul Raithby, Mojtaba Bagherzadeh, Hamed Mahmoudi, Saeed Ataie, Mohammad Bahjati, Reza Kia, Luigi Vaccaro

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

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Abstract

A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.

Original language	English
Article number	110406
Journal	Journal of Molecular Catalysis A: Chemical
Volume	474
Early online date	30 May 2019
DOIs	https://doi.org/10.1016/j.mcat.2019.110406
Publication status	Published - 1 Sept 2019

Keywords

Cross-coupling reactions
Green chemistry
Heck-Mizoroki coupling
Zwitterionic complex

ASJC Scopus subject areas

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

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10.1016/j.mcat.2019.110406

Reza Molecular Catalysis 2019 MOLCAA-D-19-00445R1.PDFAccepted author manuscript, 4 MBLicence: CC BY-NC-ND

Cite this

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title = "Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL",

abstract = "A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.",

keywords = "Cross-coupling reactions, Green chemistry, Heck-Mizoroki coupling, Zwitterionic complex",

author = "Paul Raithby and Mojtaba Bagherzadeh and Hamed Mahmoudi and Saeed Ataie and Mohammad Bahjati and Reza Kia and Luigi Vaccaro",

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doi = "10.1016/j.mcat.2019.110406",

language = "English",

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T1 - Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

AU - Raithby, Paul

AU - Bagherzadeh, Mojtaba

AU - Mahmoudi, Hamed

AU - Ataie, Saeed

AU - Bahjati, Mohammad

AU - Kia, Reza

AU - Vaccaro, Luigi

PY - 2019/9/1

Y1 - 2019/9/1

N2 - A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.

AB - A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.

KW - Cross-coupling reactions

KW - Green chemistry

KW - Heck-Mizoroki coupling

KW - Zwitterionic complex

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DO - 10.1016/j.mcat.2019.110406

M3 - Article

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JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

M1 - 110406

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Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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Applying Long-Lived Metastable States in Switchable Functionality via Kinetic Control of Molecular Assembly

Dual source (Cu and Mo) Single Crystal Diffractometer (SuperNova)

MC2- Nuclear Magnetic Resonance (NMR)

MC2- X-ray diffraction (XRD)

Cite this

Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Projects

Applying Long-Lived Metastable States in Switchable Functionality via Kinetic Control of Molecular Assembly

Equipment

Dual source (Cu and Mo) Single Crystal Diffractometer (SuperNova)

MC2- Nuclear Magnetic Resonance (NMR)

MC2- X-ray diffraction (XRD)

Cite this