Synthesis of stable polymetalated aromatic complexes through metal-macrocycle capsule-triggered cyclization.
CHEMICAL SCIENCE(2018)
摘要
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.
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