A novel Fe(III) and 2-amino-perimidinium based hybrid material catalyzed friedel–Crafts type hydroarylation of alkynes: Scope and mechanism

Preethi Raja; Priyanka Velmurugan; Chittilla Venkata Sivaram; Abir Sarbajna; Amit Ranjan Maity; Subrata Dutta; Somenath Garai; Abhaya Kumar Mishra; Debasish Mandal; Tapas Ghatak

doi:10.1016/j.molstruc.2024.138750

A novel Fe(III) and 2-amino-perimidinium based hybrid material catalyzed friedel–Crafts type hydroarylation of alkynes: Scope and mechanism

Preethi Raja, Priyanka Velmurugan, Chittilla Venkata Sivaram, Abir Sarbajna, Amit Ranjan Maity, Subrata Dutta, Somenath Garai, Abhaya Kumar Mishra, Debasish Mandal, Tapas Ghatak

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

Abstract

A new inorganic-organic hybrid material with the structural formula (C₅₁H₆₆N₉)₃[FeCl₄]·2Cl consisting of iron(III) center, 2-amino-perimidinium ligand and free chloride ions was synthesized. In addition, the compound was characterized by single-crystal X-ray diffraction and Fourier-transform infrared spectroscopy techniques. The structural arrangements and hydrogen bonding interactions in the compound were studied and successfully employed in the catalytic hydroarylation of alkynes and arenes to produce the corresponding 1,1-diaryl alkene derivatives. Gratifyingly, when nitromethane was employed as a solvent, the title compound displayed excellent catalytic activity with moderate to high conversions. Stoichiometric reactions and experimental data both provided key evidence in support of the reaction mechanism.

Original language	English
Article number	138750
Journal	Journal of Molecular Structure
Volume	1314
DOIs	https://doi.org/10.1016/j.molstruc.2024.138750
State	Published - 15 Oct 2024
Externally published	Yes

Keywords

Diarylalkenes
Friedel-crafts alkenylation
Hybrid material
Hydroarylation reaction
Hydrogen-bonds

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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10.1016/j.molstruc.2024.138750

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Raja, P., Velmurugan, P., Sivaram, C. V., Sarbajna, A., Maity, A. R., Dutta, S., Garai, S., Mishra, A. K., Mandal, D., & Ghatak, T. (2024). A novel Fe(III) and 2-amino-perimidinium based hybrid material catalyzed friedel–Crafts type hydroarylation of alkynes: Scope and mechanism. Journal of Molecular Structure, 1314, Article 138750. https://doi.org/10.1016/j.molstruc.2024.138750

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title = "A novel Fe(III) and 2-amino-perimidinium based hybrid material catalyzed friedel–Crafts type hydroarylation of alkynes: Scope and mechanism",

abstract = "A new inorganic-organic hybrid material with the structural formula (C51H66N9)3[FeCl4]·2Cl consisting of iron(III) center, 2-amino-perimidinium ligand and free chloride ions was synthesized. In addition, the compound was characterized by single-crystal X-ray diffraction and Fourier-transform infrared spectroscopy techniques. The structural arrangements and hydrogen bonding interactions in the compound were studied and successfully employed in the catalytic hydroarylation of alkynes and arenes to produce the corresponding 1,1-diaryl alkene derivatives. Gratifyingly, when nitromethane was employed as a solvent, the title compound displayed excellent catalytic activity with moderate to high conversions. Stoichiometric reactions and experimental data both provided key evidence in support of the reaction mechanism.",

keywords = "Diarylalkenes, Friedel-crafts alkenylation, Hybrid material, Hydroarylation reaction, Hydrogen-bonds",

author = "Preethi Raja and Priyanka Velmurugan and Sivaram, {Chittilla Venkata} and Abir Sarbajna and Maity, {Amit Ranjan} and Subrata Dutta and Somenath Garai and Mishra, {Abhaya Kumar} and Debasish Mandal and Tapas Ghatak",

note = "Publisher Copyright: {\textcopyright} 2024 Elsevier B.V.",

year = "2024",

month = oct,

day = "15",

doi = "10.1016/j.molstruc.2024.138750",

language = "English",

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journal = "Journal of Molecular Structure",

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T1 - A novel Fe(III) and 2-amino-perimidinium based hybrid material catalyzed friedel–Crafts type hydroarylation of alkynes

T2 - Scope and mechanism

AU - Raja, Preethi

AU - Velmurugan, Priyanka

AU - Sivaram, Chittilla Venkata

AU - Sarbajna, Abir

AU - Maity, Amit Ranjan

AU - Dutta, Subrata

AU - Garai, Somenath

AU - Mishra, Abhaya Kumar

AU - Mandal, Debasish

AU - Ghatak, Tapas

PY - 2024/10/15

Y1 - 2024/10/15

N2 - A new inorganic-organic hybrid material with the structural formula (C51H66N9)3[FeCl4]·2Cl consisting of iron(III) center, 2-amino-perimidinium ligand and free chloride ions was synthesized. In addition, the compound was characterized by single-crystal X-ray diffraction and Fourier-transform infrared spectroscopy techniques. The structural arrangements and hydrogen bonding interactions in the compound were studied and successfully employed in the catalytic hydroarylation of alkynes and arenes to produce the corresponding 1,1-diaryl alkene derivatives. Gratifyingly, when nitromethane was employed as a solvent, the title compound displayed excellent catalytic activity with moderate to high conversions. Stoichiometric reactions and experimental data both provided key evidence in support of the reaction mechanism.

AB - A new inorganic-organic hybrid material with the structural formula (C51H66N9)3[FeCl4]·2Cl consisting of iron(III) center, 2-amino-perimidinium ligand and free chloride ions was synthesized. In addition, the compound was characterized by single-crystal X-ray diffraction and Fourier-transform infrared spectroscopy techniques. The structural arrangements and hydrogen bonding interactions in the compound were studied and successfully employed in the catalytic hydroarylation of alkynes and arenes to produce the corresponding 1,1-diaryl alkene derivatives. Gratifyingly, when nitromethane was employed as a solvent, the title compound displayed excellent catalytic activity with moderate to high conversions. Stoichiometric reactions and experimental data both provided key evidence in support of the reaction mechanism.

KW - Diarylalkenes

KW - Friedel-crafts alkenylation

KW - Hybrid material

KW - Hydroarylation reaction

KW - Hydrogen-bonds

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U2 - 10.1016/j.molstruc.2024.138750

DO - 10.1016/j.molstruc.2024.138750

M3 - Article

AN - SCOPUS:85194576103

SN - 0022-2860

VL - 1314

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 138750

ER -

A novel Fe(III) and 2-amino-perimidinium based hybrid material catalyzed friedel–Crafts type hydroarylation of alkynes: Scope and mechanism

Abstract

Keywords

ASJC Scopus subject areas

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