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Herrmann's catalyst

{{Cite web |last=PubChem |title=Herrmann'S catalyst |url=https://pubchem.ncbi.nlm.nih.gov/compound/15978061 |access-date=2026-02-27 |website=pubchem.ncbi.nlm.nih.gov |language=e...

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Herrmann's catalyst is an organopalladium compound that is a popular catalyst for the Heck reaction. It is a yellow air-stable solid that is soluble in organic solvents. Under conditions for catalysis, the acetate group is lost and the Pd-C bond undergoes protonolysis, giving rise to a source of "PdP(o-tol)3".

Preparation

The complex is made by reaction of tris(o-tolyl)phosphine with palladium(II) acetate:[2]

2 Pd(OAc)2 + 2 P(o−tolyl)3 → 2 HOAc + Pd2(OAc)2[P(o−tolyl)(o−tolyl)2]2

Many analogues of Hermann's catalyst have been developed, e.g. palladacycles obtained from 2-aminobiphenyl.[3]

References

  1. ↑PubChem. "Herrmann'S catalyst". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-27.
  2. ↑Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. (1997). "Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl Halides". Chemistry – A European Journal. 3 (8): 1357–1364. Bibcode:1997ChEuJ...3.1357H. doi:10.1002/chem.19970030823.
  3. ↑Bruneau, A.; Roche, M.; Alami, M.; Messaoudi, S. (2015). "2-Aminobiphenyl Palladacycles: The "Most Powerful" Precatalysts in C–C and C–Heteroatom Cross-Couplings". ACS Catalysis. 5 (2): 1386–1396. doi:10.1021/cs502011x.