Highly Active Palladium Catalyst Applicable to Various Coupling Reactions

Organ’s catalyst (1) is a palladium catalyst developed by Organ et al.^1,2) 1 contains an NHC ligand and shows high catalytic activity in Suzuki-Miyaura cross-coupling, Negishi coupling and Buchwald-Hartwig amination reactions. In addition, a coupling product can be obtained in a high yield even with a small amount of catalyst as shown in the following example. Therefore, 1 is expected to be widely used as a catalyst for coupling reactions in drug discovery research and material development.

TCI Practical Example: Synthesis of 2 using 1
To a 100 mL 4-neck flask under nitrogen atmosphere, 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (1.10 g, 3.20 mmol), 4-(9H-carbazol-9-yl)phenylboronic acid pinacol ester (1.42 g, 3.85 mmol, 1.2 eq), potassium carbonate (0.89 g, 6.40 mmol), THF (20 mL), water (8 mL), 1 (2.2 mg, 3.2 µmol, 0.1 mol%) were added, and the reaction mixture was refluxed for 1 hour. After confirming the disappearance of the raw material, the reaction mixture was cooled to room temperature, and then water (20 mL) was added and the precipitated solid was filtered out. The obtained crude product was filtered through a short pad of silica gel using CH₂Cl₂ as eluent and the filtrate was evaporated in vacuo to give a white solid. The solid was washed with methanol to give 2 (1.70 g, 96% yield) as a white powder.

References

• 1) Easily Prepared Air- and Moisture-Stable Pd–NHC (NHC=N-Heterocyclic Carbene) Complexes: A Reliable, User-Friendly, Highly Active Palladium Precatalyst for the Suzuki–Miyaura Reaction
  • C. J. O'Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J. 2006, 12, 4743.
• 2) Pd-Catalyzed Aryl Amination Mediated by Well Defined, N-Heterocyclic Carbene (NHC)-Pd Precatalysts, PEPPSI
  • M. G. Organ, M. Abdel-Hadi, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, M. Sayah, C. Valente, Chem. Eur. J. 2008, 14, 2443.

Related Compounds

T3452

4-(9H-Carbazol-9-yl)phenylboronic Acid Pinacol Ester

B5803

2-([1,1'-Biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine

P1748

Potassium Carbonate

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