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Issue 33, 2019
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Synthesis and structural characterization of 20-membered macrocyclic rings bearing trans-chelating bis(N-heterocyclic carbene) ligands and the catalytic activity of their palladium(ii) complexes

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Abstract

Macrocycles consisting of a 20-membered ring containing two imidazolium salt functionalities and of the formula [PhCH2N(CH2CH2CH2)Im(CH2CH2CH2)2][Br]2 (Im = imidazole = 3a, benzimidazole = 3b) were synthesized in 70–75% yields. These salts serve as precursors to macrocycles containing two N-heterocyclic carbene (NHC) moieties. Reaction of the macrocyclic salts 3a and 3b with silver oxide afforded macrocyclic-bis(NHC)silver(I) complexes 4a and 4b. Single-crystal X-ray diffraction studies of macrocyclic-bis(NHC)silver(I) complex 4a revealed a tetranuclear silver core with a short Ag–Ag distance (2.9328 Å). Complexes 4a and 4b serve as carbene transfer reagents to Pd. The treatment of macrocyclic-bis(NHC)silver(I) complexes 4a and 4b with one equivalent of PdCl2(MeCN)2 in methylene chloride afforded square-planar trans-macrocyclic-bis(NHC)Pd(II)X2 complexes 5a and 5b. Preliminary screening of these palladium complexes showed they are competent precatalysts for Heck and Suzuki coupling reactions.

Graphical abstract: Synthesis and structural characterization of 20-membered macrocyclic rings bearing trans-chelating bis(N-heterocyclic carbene) ligands and the catalytic activity of their palladium(ii) complexes

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Publication details

The article was received on 21 May 2019, accepted on 23 Jul 2019 and first published on 23 Jul 2019


Article type: Paper
DOI: 10.1039/C9DT02147G
Dalton Trans., 2019,48, 12577-12590

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    Synthesis and structural characterization of 20-membered macrocyclic rings bearing trans-chelating bis(N-heterocyclic carbene) ligands and the catalytic activity of their palladium(II) complexes

    R. Thapa and S. M. Kilyanek, Dalton Trans., 2019, 48, 12577
    DOI: 10.1039/C9DT02147G

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