Herrmann's catalyst

Last updated
Herrmann's catalyst
HerrmannCat.png
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 681-425-4
PubChem CID
UNII
  • InChI=1S/2C21H20P.2C2H4O2.2Pd/c2*1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;2*1-2(3)4;;/h2*4-15H,1H2,2-3H3;2*1H3,(H,3,4);;/q2*-1;;;2*+2/p-2
    Key: AQTSNKXEMWZOGA-UHFFFAOYSA-L
  • CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC(=O)[O-].CC(=O)[O-].[Pd+2].[Pd+2]
Properties
C46H46O4P2Pd2
Molar mass 937.66 g·mol−1
AppearanceYellow solid
Melting point 123–125 °C (253–257 °F; 396–398 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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".

The complex is made by reaction of tris(o-tolyl)phosphine with palladium(II) acetate: [1]

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. [2]

References

  1. ↑ 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.
  2. ↑ 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.
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