Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions

The treatment of 2-(ArNC(H))C(6)H(4)-HNC(9)H(6)N with n-BuLi and the subsequent addition of CuCl(2) afforded the anilido-aldimine Cu(II) complexes 1-5 Cu[{2-[ArN=C(H)]C(6)H(4)}N(8-C(9)H(6)N)]Cl (Ar = 2,6-(i)Pr(2)C(6)H(3) (1), 2,4,6-(CH(3))(3)C(6)H(2) (2), 4-OCH(3)C(6)H(4) (3), 4-BrC(6)H(4) (4), 4-Cl...

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Autores principales: Zhou, Xiaoyu, Yang, Jiaxin, Hao, Zhiqiang, Han, Zhangang, Lin, Jin, Lu, Guo-Liang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10647278/
https://www.ncbi.nlm.nih.gov/pubmed/37959825
http://dx.doi.org/10.3390/molecules28217406
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author Zhou, Xiaoyu
Yang, Jiaxin
Hao, Zhiqiang
Han, Zhangang
Lin, Jin
Lu, Guo-Liang
author_facet Zhou, Xiaoyu
Yang, Jiaxin
Hao, Zhiqiang
Han, Zhangang
Lin, Jin
Lu, Guo-Liang
author_sort Zhou, Xiaoyu
collection PubMed
description The treatment of 2-(ArNC(H))C(6)H(4)-HNC(9)H(6)N with n-BuLi and the subsequent addition of CuCl(2) afforded the anilido-aldimine Cu(II) complexes 1-5 Cu[{2-[ArN=C(H)]C(6)H(4)}N(8-C(9)H(6)N)]Cl (Ar = 2,6-(i)Pr(2)C(6)H(3) (1), 2,4,6-(CH(3))(3)C(6)H(2) (2), 4-OCH(3)C(6)H(4) (3), 4-BrC(6)H(4) (4), 4-ClC(6)H(4) (5)), respectively. All the copper complexes were fully characterized by IR, EPR and HR-MS spectra. The X-ray diffraction analysis reveals that 2 and 4 are mononuclear complexes, and the Cu atom is sitting in a slightly square-planar geometry. These Cu(II) complexes have exhibited excellent catalytic activity in the Chan–Lam coupling reactions of benzimidazole derivatives with arylboronic acids, achieving the highest yields of up to 96%.
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spelling pubmed-106472782023-11-03 Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions Zhou, Xiaoyu Yang, Jiaxin Hao, Zhiqiang Han, Zhangang Lin, Jin Lu, Guo-Liang Molecules Article The treatment of 2-(ArNC(H))C(6)H(4)-HNC(9)H(6)N with n-BuLi and the subsequent addition of CuCl(2) afforded the anilido-aldimine Cu(II) complexes 1-5 Cu[{2-[ArN=C(H)]C(6)H(4)}N(8-C(9)H(6)N)]Cl (Ar = 2,6-(i)Pr(2)C(6)H(3) (1), 2,4,6-(CH(3))(3)C(6)H(2) (2), 4-OCH(3)C(6)H(4) (3), 4-BrC(6)H(4) (4), 4-ClC(6)H(4) (5)), respectively. All the copper complexes were fully characterized by IR, EPR and HR-MS spectra. The X-ray diffraction analysis reveals that 2 and 4 are mononuclear complexes, and the Cu atom is sitting in a slightly square-planar geometry. These Cu(II) complexes have exhibited excellent catalytic activity in the Chan–Lam coupling reactions of benzimidazole derivatives with arylboronic acids, achieving the highest yields of up to 96%. MDPI 2023-11-03 /pmc/articles/PMC10647278/ /pubmed/37959825 http://dx.doi.org/10.3390/molecules28217406 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhou, Xiaoyu
Yang, Jiaxin
Hao, Zhiqiang
Han, Zhangang
Lin, Jin
Lu, Guo-Liang
Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions
title Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions
title_full Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions
title_fullStr Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions
title_full_unstemmed Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions
title_short Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions
title_sort copper complexes with n,n,n-tridentate quinolinyl anilido-imine ligands: synthesis and their catalytic application in chan−lam reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10647278/
https://www.ncbi.nlm.nih.gov/pubmed/37959825
http://dx.doi.org/10.3390/molecules28217406
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