2015
DOI: 10.1039/c4dt03324h
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Synthesis, characterization, photophysical properties, and catalytic activity of an SCS bis(N-heterocyclic thione) (SCS-NHT) Pd pincer complex

Abstract: Treatment of 1,3-bis(3'-butylimidazolyl-1'-yl)benzene diiodide with elemental sulfur in the presence of a base produced a bis(N-heterocyclic thione) (NHT) pincer ligand precursor. Its reaction with PdCl2(CH3CN)2 produced chloro[1,3-bis(3'-butylimidazole-2'-thione-κ-S)benzene-κ-C]palladium(ii), a 6,6-fused ring SCS-NHT palladium pincer complex. This air stable compound is, to our knowledge, the first SCS pincer complex that utilizes N-heterocyclic thione (NHT) donor groups. The molecular structures of the ligan… Show more

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Cited by 42 publications
(73 citation statements)
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References 82 publications
(130 reference statements)
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“…The imidazolium-based NHC precursors can also be converted into thiourea derivatives [ 26 ], featuring a soft S-donor for metal coordination. Such thiones are good σ-donors and weak π-acceptors and a wide range of metal complexes have been synthesized, often for investigations into their catalytic properties [ 26 , 27 , 28 , 29 , 30 , 31 ]. As with thiones [ 32 , 33 , 34 , 35 ], some of their metal complexes have shown biological activity.…”
Section: Introductionmentioning
confidence: 99%
“…The imidazolium-based NHC precursors can also be converted into thiourea derivatives [ 26 ], featuring a soft S-donor for metal coordination. Such thiones are good σ-donors and weak π-acceptors and a wide range of metal complexes have been synthesized, often for investigations into their catalytic properties [ 26 , 27 , 28 , 29 , 30 , 31 ]. As with thiones [ 32 , 33 , 34 , 35 ], some of their metal complexes have shown biological activity.…”
Section: Introductionmentioning
confidence: 99%
“…have reported a series of bis (imidazolin‐2‐thione) analogues Btb (Table 1), [ 21 ] and a syn orientation was reported for n Bu‐ Btb . [ 21a ] The calculated C‐S bond distances up to 1.6975 Å is close to the typical C‐S partial double bond distance (1.72 Å), [ 22 ] and thus the thiocarbonyl moieties of 3a / 3b are better described as partial double bonds. In addition, the C‐S bond lengths of 3a / 3b are slightly longer than those for n Bu‐ Btb indicating a less pronounced C‐S double bond character in the former case.…”
Section: Resultsmentioning
confidence: 99%
“…have reported the cyclopalladations of Btb (Scheme 5), in which cases NaOAc was not utilized. [ 21 ] As such, 3a was used as a representative, and under Hollis's condition, the metalation reactivity in the absence of NaOAc was examined. 1 H NMR spectrum of the as‐formed product shows a very downfield singlet at 12.17 ppm, which is tentatively assigned to the C aryl ‐H a proton of non‐cyclopalladated complex 7a .…”
Section: Resultsmentioning
confidence: 99%
“…The reported catalysts and conditions for optimum performance are as follows. The important reaction conditions for each species follow it in parentheses: benzimidazole based Pd(II) NHC complex (1 mol%, 100 °C), palladium‐1,3,5‐triaza‐7‐phosphaadamantane complex (1‐2.5 mol%, 24 h), Pd(II) complexes of bis‐NHC based (C, N, C) pincers (1 mol%, 140 °C, 4 h), and palladium complex of (S, C, S) pincer (2 mol%, CuI, 18 h) . Thus performance of 1–4 is better relative to these reported systems.…”
Section: Resultsmentioning
confidence: 99%