BINAP-Palladium Photocatalyst

  • Author: ChemistryViews.org
  • Published: 22 January 2016
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Dalton Transactions/Royal Society of Chemistry (RSC)
  • Associated Societies: Royal Society of Chemistry (RSC), UK
thumbnail image: BINAP-Palladium Photocatalyst

Chiral BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) ligands play an important role in asymmetric organic catalysis. Due to their electronic structure, however, they can also absorb light in the UV-Vis region of the spectrum and be useful in photochemical processes.


Akiko Inagaki and Changsu Son, Tokyo Metropolitan University, Japan, have developed a photoactive palladium complex with a BINAP ligand, modified with 2-naphthyl substituents on the phosphor atoms. The complex was synthesized by adding (cod)PdMeCl (cod = 1,5-cyclooctadiene) to a solution of the BINAP-based ligand, and subsequent remvoal of a chloride ion using the silver salt AgBF4.


The palladium complex shows photocatalytic activity for the polymerization of styrenes and its activity can be switched on and off using light. The 2-naphthyl groups improve the light absorption of the complex due to their aromatic character. The researchers propose a reaction mechanism that involves the generation of an intermediate hydride complex and insertion of the monomer into the Pd–H bond. Further monomer insertions produce the polymer, and a final β-hydride elimination relases the product. According to the team, irradiation with light probably accelarates the insertion steps, which allows the control of the reaction.


 

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