Jump to main content
Jump to site search


NHC Hg(II) and Pd(II) complexes based on 1,8-dihydroxy-9,10-anthraquinone: synthesis, structure and catalysis

Author affiliations

Abstract

Three bis-azolium salts, 1,8-bis[3′-(N-R-azoliumyl)propoxy]-9,10-anthraquinone hexafluorophosphate L1H2(PF6)2L2H2(PF6)2 (R = ethyl or picolyl, azoliumyl = imidazoliumyl or benzimidazoliumyl) and 1,3-bis[8′-(3′′-(N-ethyl-imidazoliumyl)propoxy)anthraquinon-l-yloxy]propane hexafluorophosphate (L3H2(PF6)2), as well as their three macrometallocycle N-heterocyclic carbene mercury(II) complexes [L1′HgBr2] (1), [L2Hg](PF6)2 (3) and [L3Hg](PF6)2 (3) were prepared and characterized by 1H NMR and 13C NMR spectroscopy and X-ray crystallography. In complexes 1–3, each macrometallocycle (18-membered macrometallocycle for 1, one 18-membered and two 6-membered macrometallocycles for 2, and 28-membered macrometallocycle for 3) was formed by one biscarbene ligand (L1′ for 1, L2 for 2, and L3 for 3) and one Hg(II) ion. Interestingly, the carbonyl group on the 9-position in complex 1 reacted with two acetonitrile molecules in the presence of the strong base KOtBu through losing one molecule of H2O to form L1′. As a result, two –CH2CN units were introduced to anthraquinone, in which the two –CH2CN units lie on two flanks of the anthraquinone plane. In the crystal packings of 1–3, 2D supramolecular layers and 3D supramolecular frameworks are formed via hydrogen bonds and π⋯π interactions. Additionally, the catalytic activity of the L1–Pd(II) complex in situ in the Suzuki–Miyaura reaction was studied. The results show that this catalyst is efficient in the Suzuki–Miyaura reaction.

Graphical abstract: NHC Hg(ii) and Pd(ii) complexes based on 1,8-dihydroxy-9,10-anthraquinone: synthesis, structure and catalysis

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Apr 2018, accepted on 03 Jul 2018 and first published on 04 Jul 2018


Article type: Paper
DOI: 10.1039/C8NJ02029A
Citation: New J. Chem., 2018, Advance Article
  •   Request permissions

    NHC Hg(II) and Pd(II) complexes based on 1,8-dihydroxy-9,10-anthraquinone: synthesis, structure and catalysis

    Z. Zhao, Z. Hu, S. Yu and Q. Liu, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ02029A

Search articles by author

Spotlight

Advertisements