Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions
Abstract
:1. Introduction
2. Carbon–Carbon Coupling Reactions
2.1. Mizoroki–Heck Reaction
2.2. Suzuki–Miyaura and Related Reactions
2.3. Sonogashira and Related Reactions
2.4. Kumada–Tamao–Corriu Reaction
3. Carbon–Heteroatom Coupling Reactions
4. Immobilised and Heterogeneous Catalysts
5. Future Prospects
Author Contributions
Funding
Conflicts of Interest
References
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Metal | T (°C) | Solvent | Time (h) | Ligand 2 | Base | Catalyst (mol%) | Yield (%) | Ref. |
---|---|---|---|---|---|---|---|---|
Pd | 150 | DMF | 24 | O,N,S | NaOAc | 0.1 | 46–95 | [15] |
Pd | 130–145 | DMF | 24–36 | O,N,S | Na2CO3 | 0.1–1.0 | 50–90 | [94] |
Pd | 110–150 | EtOH/toluene or PEG | 12–48 | N,S | Cs2CO3 | 0.5–1.0 | 57–80 | [95] |
Pd | 100 | DMF | 8 | N,S | K2CO3 | 0.01 | 60–97 | [96] |
Ni | 130 | DMF | 24 | O,N,S | Cs2CO3 | 2.0 | 36–99 | [97] |
Ni | 110 | DMF | 24 | N,S | K2CO3 | 0.5 | 60–94 | [98] |
Pd | 120 | DMF | 5–24 | S,N,N,S | Et3N | 3.5 | 67–82 3 | [99] |
Metal | T (°C) | Solvent | Time (h) | Ligand 2 | Base | Catalyst (mol%) | Yield (%) | Ref. |
---|---|---|---|---|---|---|---|---|
Pd | 100 | DMF/H2O | 24 | O,N,S | Na2CO3 | 0.1 | 40–88 | [16] |
Pd | 100–157 | DMF/H2O | 0.25–1 | O,N,S | Na2CO3 | 0.001–0.1 | 25–85 | [100] 3 |
Pd | 25–95 | EtOH/toluene | 9–20 | N,S | NaOH | 0.001 | >99 | [102] |
Pd | 140 | DMF | 24 | O,N,S | K2CO3 | 2.0 | 46–78 | [103] |
Pd | 120 | PEG | 6–24 | N,S | NaOH or Cs2CO3 | 0.001 | 100 | [106] |
Pd | 120 | PEG | 6–24 | N,S | NaOH | 0.001 | 65–100 | [107] |
Pd | 120 | PEG | 4–24 | C,N,S | NaOH | 0.001 | 71–100 | [107] |
Pd | 25–95 | EtOH/toluene | 9–20 | N,S | NaOH | 0.001 | 98–100 | [108] |
Pd | 25–95 | EtOH/toluene | 3–14 | C,N,S | NaOH | 0.001 | 100 | [108] |
Pd | 130 | DMF | 24–48 | C,N,S | K3PO4 | 0.5 | 31–99 | [109] |
Pd | reflux | DMF | 3 | O,N,S | K2CO3 | 0.001 | 78–99 | [110] |
Pd | 25 | EtOH | 0.5–1.5 | N,S | K2CO3 | 0.2 | 76–98 | [111] 4 |
Pd | 100 | DMF | 24 | N,S | K2CO3 | 0.05 | 60–99 | [112] |
Pd | 70 | H2O | 24 | O,N,S | Na2CO3 | 1.0 | 25–98 | [113] |
Pd | 28 | H2O | 2–12 | N,S | K2CO3 | 1.18 | 65–90 | [114] |
Pd | 60–70 | EtOH/H2O | 1–4 | C,N,S | K2CO3 | 0.125 | 51–99 | [115] |
Pd | 95 | EtOH/toluene | 6–8 | N,S | Cs2CO3 | 0.001 | 79–100 | [117] |
Ni | 140 | DMF | 24 | O,N,S | Cs2CO3 | 2.0 | 40–99 | [118] |
Ni | 90 | DMA | 7 | O,N,S | K2CO3 | 1.0 | 28–64 | [119] |
Pd | 110 | toluene | 12 | N,S | Cs2CO3 | 5.0 | 62–97 | [120] 5 |
Metal | T (°C) | Solvent | Time (h) | Ligand 2 | Base | Catalyst (mol%) | Yield (%) | Ref. |
---|---|---|---|---|---|---|---|---|
Pd | 75–110 | EtOH/toluene or PEG | 10–15 | N,S | NaOH | 0.5 | 68–99 | [95] |
Pd | 80 | Et3N | 8 | N,S | Et3N | 0.5 | 65 | [111] |
Pd | rt | DMF | 12 | N,S | Et3N | 0.5 | 67–99 | [122] |
Ni | 70 | MeOH | 4 | O,N,S | pyridine | 0.5 | 55–85 | [119] |
Ni | 80 | DMF | 8 | N,S | Et3N | 0.1 | 79–99 | [123] |
Pd | 35 | CH2Cl2 | 24 | O,N,S | KOAc | 2.0 | 30–99 | [124] 3 |
Metal | Substrates | T (°C) | Solvent | Time (h) | Ligand 1 | Base | Catalyst (mol%) | Yield (%) | Ref. |
---|---|---|---|---|---|---|---|---|---|
Pd | ArBr + 2ary amine | 145 | PEG | 24 | N,S | NaOBut | 1.0 | 50–62 | [106] |
Pd | ArBr + 1ary/2ary amine | 145 | PEG | 24 | N,S | NaOBut | 0.1 | 100 | [107] |
Pd | ArBr + 1ary/2ary amine | 145 | PEG | 18 | C,N,S | NaOBut | 0.1 | 100 | [107] |
Pd | ArBr + aniline | 105 | toluene | 12–18 | C,N,S | NaOBut | 0.01 | 100 | [108] |
Pd | (het)ArBr + 2ary amine | 100 | 2-BuOH | 24 | N,S | K2CO3 | 0.2 | 77–99 | [137] |
Pd | (het)ArBr + N-heterocycle | 110 | DMSO | 10 | O,N,S | KOH | 0.75 | 75–90 | [138] |
Cu | ArBr + N-heterocycle | 110 | DMF | 24 | O,N,S | K2CO3 | 10.0 | 42–56 | [139] |
Cu | (het)ArB(OH)2 + aniline | r.t. | DMF/H2O | 14–18 | N,S | Et3N | 10.0 | 74–95 | [140] |
Cu | (het)ArB(OH)2 + N-heterocycle | r.t. | DMF/H2O | 18–24 | N,S | Et3N | 10.0 | 70–94 | [140] |
Cu | RCH2OH + 1ary amine | 100 | toluene | 12 | P,N,S | KOH | 0.1–0.2 | 89–99 | [141] |
Ru | RCH2OH + aniline | 100 | none | 6 | O,N,S | KOBut | 1.0 | 61–86 | [74] |
Ru | RCH2OH + 1ary amine | 100 | toluene | 12–24 | P,N,S | KOH | 0.5–1.0 | 45–99 | [142] |
Ru | RCH2OH + 1ary amine | 100 | toluene | 12 | P,N,S | KOH | 0.5 | 79–98 | [143] |
Ru | RCH2OH + 1ary amine | 100 | toluene | 12 | P,N,S | KOH | 0.5 | 59–98 | [144] |
Ru | RCH2OH + sulfonamide | 120 | toluene | 12 | P,N,S | KOH | 0.5 | 21–99 | [144] |
Pd | ArBr/ArI + p-cresol | 80 | DMF | 12 | N,S | K2CO3 | 1.0 | 62–94 | [146] |
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Kostas, I.D.; Steele, B.R. Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions. Catalysts 2020, 10, 1107. https://doi.org/10.3390/catal10101107
Kostas ID, Steele BR. Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions. Catalysts. 2020; 10(10):1107. https://doi.org/10.3390/catal10101107
Chicago/Turabian StyleKostas, Ioannis D., and Barry R. Steele. 2020. "Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions" Catalysts 10, no. 10: 1107. https://doi.org/10.3390/catal10101107