Synthesis and characterization of copper(I) compounds incorporating pyrazole-derived ligands: A study on carbon-carbon coupling reaction

Chen Yi Li; Yu Ling Lien; Jayaramann Vinayagam; Amitabha Datta; Ting Chia Hu; Chia Her Lin; Jui Hsien Huang

doi:10.1016/j.ica.2015.07.018

Synthesis and characterization of copper(I) compounds incorporating pyrazole-derived ligands: A study on carbon-carbon coupling reaction

Chen Yi Li
, Yu Ling Lien
, Jayaramann Vinayagam
, Amitabha Datta
, Ting Chia Hu
, Chia Her Lin
, Jui Hsien Huang^*

^*Corresponding author for this work

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

3 Citations (Scopus)

Abstract

A series of copper(I) compounds manifesting with the pyrazole mediated precursor, ArN[CH₂(C₃H₃N₂)]₂ (Ar = 2,6-diisopropylphenyl) (LN3), were synthesized conveniently and treatment of the derivatives with small organic molecules like pyrazine and triphenylphosphine were analyzed. Reacting one and two equivalents of LN3 with [Cu(CH₃CN)₄]PF₆ in CH₃CN at room temperature afforded [Cu(LN3)(CH₃CN)₂]PF₆ (1) and [Cu(LN3)₂]PF₆ (2), respectively in high yield. Similarly, while reacting one equivalent of LN3 and CuI in acetonitrile for 12 h, produced a white solid, [Cu(LN3)]I (3). Furthermore, by adding one or two equivalents of PPh₃ into compound 1, using methylene chloride as solvent rendered [Cu(LN3)(PPh₃)]PF₆ (4) and [Cu(LN3)(PPh₃)₂]PF₆ (5), respectively, in satisfactory yield. In addition, compound {[Cu(LN3)(C₄H₄N₂)]₂(PF₆)₂}_n (6) was generated as one-dimensional polymer by treating compound 1 and pyrazine in THF at room temperature. All the Cu(I)-derivatives were characterized by ¹H and ¹³C NMR spectroscopy and the molecular structures (1, 4, and 6) were determined by single crystal X-ray diffraction. Additionally, the catalytic reactions of Sonogashira type C-C coupling were discussed using compounds 2, 3, 5, and 6 as catalysts.

Original language	English
Pages (from-to)	327-334
Number of pages	8
Journal	Inorganica Chimica Acta
Volume	435
DOIs	https://doi.org/10.1016/j.ica.2015.07.018
Publication status	Published - 2015 Aug 1
Externally published	Yes

Keywords

Carbon-carbon coupling
Copper(I)
Pyrazole-derived ligands

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.ica.2015.07.018

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@article{68b487f0cc3b4cc7b74568582063e2b5,

title = "Synthesis and characterization of copper(I) compounds incorporating pyrazole-derived ligands: A study on carbon-carbon coupling reaction",

abstract = "A series of copper(I) compounds manifesting with the pyrazole mediated precursor, ArN[CH2(C3H3N2)]2 (Ar = 2,6-diisopropylphenyl) (LN3), were synthesized conveniently and treatment of the derivatives with small organic molecules like pyrazine and triphenylphosphine were analyzed. Reacting one and two equivalents of LN3 with [Cu(CH3CN)4]PF6 in CH3CN at room temperature afforded [Cu(LN3)(CH3CN)2]PF6 (1) and [Cu(LN3)2]PF6 (2), respectively in high yield. Similarly, while reacting one equivalent of LN3 and CuI in acetonitrile for 12 h, produced a white solid, [Cu(LN3)]I (3). Furthermore, by adding one or two equivalents of PPh3 into compound 1, using methylene chloride as solvent rendered [Cu(LN3)(PPh3)]PF6 (4) and [Cu(LN3)(PPh3)2]PF6 (5), respectively, in satisfactory yield. In addition, compound \{[Cu(LN3)(C4H4N2)]2(PF6)2\}n (6) was generated as one-dimensional polymer by treating compound 1 and pyrazine in THF at room temperature. All the Cu(I)-derivatives were characterized by 1H and 13C NMR spectroscopy and the molecular structures (1, 4, and 6) were determined by single crystal X-ray diffraction. Additionally, the catalytic reactions of Sonogashira type C-C coupling were discussed using compounds 2, 3, 5, and 6 as catalysts.",

keywords = "Carbon-carbon coupling, Copper(I), Pyrazole-derived ligands",

author = "Li, \{Chen Yi\} and Lien, \{Yu Ling\} and Jayaramann Vinayagam and Amitabha Datta and Hu, \{Ting Chia\} and Lin, \{Chia Her\} and Huang, \{Jui Hsien\}",

year = "2015",

month = aug,

day = "1",

doi = "10.1016/j.ica.2015.07.018",

language = "English",

volume = "435",

pages = "327--334",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - Synthesis and characterization of copper(I) compounds incorporating pyrazole-derived ligands

T2 - A study on carbon-carbon coupling reaction

AU - Li, Chen Yi

AU - Lien, Yu Ling

AU - Vinayagam, Jayaramann

AU - Datta, Amitabha

AU - Hu, Ting Chia

AU - Lin, Chia Her

AU - Huang, Jui Hsien

PY - 2015/8/1

Y1 - 2015/8/1

N2 - A series of copper(I) compounds manifesting with the pyrazole mediated precursor, ArN[CH2(C3H3N2)]2 (Ar = 2,6-diisopropylphenyl) (LN3), were synthesized conveniently and treatment of the derivatives with small organic molecules like pyrazine and triphenylphosphine were analyzed. Reacting one and two equivalents of LN3 with [Cu(CH3CN)4]PF6 in CH3CN at room temperature afforded [Cu(LN3)(CH3CN)2]PF6 (1) and [Cu(LN3)2]PF6 (2), respectively in high yield. Similarly, while reacting one equivalent of LN3 and CuI in acetonitrile for 12 h, produced a white solid, [Cu(LN3)]I (3). Furthermore, by adding one or two equivalents of PPh3 into compound 1, using methylene chloride as solvent rendered [Cu(LN3)(PPh3)]PF6 (4) and [Cu(LN3)(PPh3)2]PF6 (5), respectively, in satisfactory yield. In addition, compound {[Cu(LN3)(C4H4N2)]2(PF6)2}n (6) was generated as one-dimensional polymer by treating compound 1 and pyrazine in THF at room temperature. All the Cu(I)-derivatives were characterized by 1H and 13C NMR spectroscopy and the molecular structures (1, 4, and 6) were determined by single crystal X-ray diffraction. Additionally, the catalytic reactions of Sonogashira type C-C coupling were discussed using compounds 2, 3, 5, and 6 as catalysts.

AB - A series of copper(I) compounds manifesting with the pyrazole mediated precursor, ArN[CH2(C3H3N2)]2 (Ar = 2,6-diisopropylphenyl) (LN3), were synthesized conveniently and treatment of the derivatives with small organic molecules like pyrazine and triphenylphosphine were analyzed. Reacting one and two equivalents of LN3 with [Cu(CH3CN)4]PF6 in CH3CN at room temperature afforded [Cu(LN3)(CH3CN)2]PF6 (1) and [Cu(LN3)2]PF6 (2), respectively in high yield. Similarly, while reacting one equivalent of LN3 and CuI in acetonitrile for 12 h, produced a white solid, [Cu(LN3)]I (3). Furthermore, by adding one or two equivalents of PPh3 into compound 1, using methylene chloride as solvent rendered [Cu(LN3)(PPh3)]PF6 (4) and [Cu(LN3)(PPh3)2]PF6 (5), respectively, in satisfactory yield. In addition, compound {[Cu(LN3)(C4H4N2)]2(PF6)2}n (6) was generated as one-dimensional polymer by treating compound 1 and pyrazine in THF at room temperature. All the Cu(I)-derivatives were characterized by 1H and 13C NMR spectroscopy and the molecular structures (1, 4, and 6) were determined by single crystal X-ray diffraction. Additionally, the catalytic reactions of Sonogashira type C-C coupling were discussed using compounds 2, 3, 5, and 6 as catalysts.

KW - Carbon-carbon coupling

KW - Copper(I)

KW - Pyrazole-derived ligands

UR - https://www.scopus.com/pages/publications/84938599882

UR - https://www.scopus.com/pages/publications/84938599882#tab=citedBy

U2 - 10.1016/j.ica.2015.07.018

DO - 10.1016/j.ica.2015.07.018

M3 - Article

AN - SCOPUS:84938599882

SN - 0020-1693

VL - 435

SP - 327

EP - 334

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

ER -

Synthesis and characterization of copper(I) compounds incorporating pyrazole-derived ligands: A study on carbon-carbon coupling reaction

Abstract

Keywords

ASJC Scopus subject areas

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