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 - 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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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 -