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Synthesis of stable polymetalated aromatic complexes through metal–macrocycle capsule-triggered cyclization

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Abstract

Polymetalated aromatic compounds are of great interest because of their intermediate roles in many organic transformations. However, they are elusive and synthetically challenging. In this study, a dynamic coordination capsule constructed by a flexible macrocycle and silver(I) ions is applied to trigger one-step or cascade cyclization reactions for various alkyne substrates, finally leading to five unprecedented polysilver heteroaromatic intermediates (including indole, quinoline, benzocarbazole and 2,2′-biindole). The acquired heteroaromatic species is doubly charged, particularly at vicinal positions, and each is surrounded by a tetrasilver aggregate. The metal–macrocycle capsule holds a great potential of flexibly adjusting its conformation to adapt different polysilver heteroaromatic species. DFT calculations further reveal that metal-perturbed aromaticity and multi-centered bonding both contribute to stabilization of the polysilver heteroaromatic complexes.

Graphical abstract: Synthesis of stable polymetalated aromatic complexes through metal–macrocycle capsule-triggered cyclization

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Publication details

The article was received on 17 Oct 2017, accepted on 02 Dec 2017 and first published on 04 Dec 2017


Article type: Edge Article
DOI: 10.1039/C7SC04503D
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Synthesis of stable polymetalated aromatic complexes through metal–macrocycle capsule-triggered cyclization

    X. He, Y. Xue, C. Li, Y. Wang, H. Jiang and L. Zhao, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04503D

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