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

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

3 Scopus citations

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 (US)
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
State	Published - Aug 1 2015
Externally published	Yes

Bibliographical note

Funding Information:
We acknowledge the financial assistance from the Ministry of Science and Technology of Taiwan . We would also like to thank the National Changhua University of Education for providing the facility of X-ray diffractometer and NMR spectrometer.

Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.

Keywords

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

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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}",

note = "Funding Information: We acknowledge the financial assistance from the Ministry of Science and Technology of Taiwan . We would also like to thank the National Changhua University of Education for providing the facility of X-ray diffractometer and NMR spectrometer. Publisher Copyright: {\textcopyright} 2015 Elsevier B.V. All rights reserved.",

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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

N1 - Funding Information: We acknowledge the financial assistance from the Ministry of Science and Technology of Taiwan . We would also like to thank the National Changhua University of Education for providing the facility of X-ray diffractometer and NMR spectrometer. Publisher Copyright: © 2015 Elsevier B.V. All rights reserved.

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

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JF - Inorganica Chimica Acta

ER -

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

Abstract

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Keywords

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