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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.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Thapa, Rajesh Kilyanek, Stefan M. |
| Copyright Year | 2019 |
| 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. |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c9dt02147g |
| PubMed reference number | 31368475 |
| Journal | Medline |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c9/dt/c9dt02147g/c9dt02147g1.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/c9dt02147g |
| Journal | Dalton transactions |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
