Suzuki-Miyaura Cross Coupling Catalyzed by Cost-Effective Nickel Salt

Nickel chloride (II) hexahydrate (1) is utilized as a catalyst for Suzuki-Miyaura cross coupling reaction.¹⁾ In presence of 1 and a ligand, the reaction with aryl boronic acids and arylhalides leads to corresponding biaryl compounds in moderate to good yields.²⁾ This reaction is also applicable to heteroaryl compounds as substrates and in gram scale synthesis. Depending on substrates, the ligand can be chosen from ligand library while in most cases 1,1'-bis(diphenylphosphino)ferrocene (DPPF) and 1,3-bis(dicyclohexylphosphino)propane (DCPP) are suitable. Furthermore, methanol is found to improve conversion. This reaction is expected to be a powerful solution for cost-effective and sustainable processes.

Related Products

N0851

Nickel Chloride (II) Hexahydrate

B2027

1,1'-Bis(diphenylphosphino)ferrocene

D1270

DBU

References

• 1) Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
  • N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
• 2) Advancing Base-Metal Catalysis: Development of a Screening Method for Nickel-Catalyzed Suzuki-Miyaura Reactions of Pharmaceutically Relevant Heterocycles
  • M. J. Goldfogel, X. Guo, J. L. M. Matos, J. A. Gurak, Jr., M. V. Joannou, W. B. Moffat, E. M. Simmons, S. R. Wisniewski, Org. Proc. Res. Dev. 2021, ASAP.

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