Herrmann's catalyst

Herrmann's catalyst
Identifiers
CAS Number	172418-32-5;
ChemSpider	10136140;
PubChem CID	15978061;
UNII	0K4FY6KS4N;
CompTox Dashboard (EPA)	DTXSID40704833 ;
Properties
Chemical formula	C46H46O4P2Pd2
Molar mass	937.66 g·mol−1
Appearance	yellow solid
Melting point	123-125 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

{\begin{aligned}&{\ce {2 Pd(OAc)2 + 2 P(C6H4-2-CH3)3 ->}}\\&{\ce {2 HOAc + Pd2(OAc)2[P(C6H4-2-CH2)(C6H4-2-CH3)2]2}}\end{aligned}}

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

References

↑ 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: 1357–1364. doi:10.1002/chem.19970030823.
↑ 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: 1386–1396. doi:10.1021/cs502011x.

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[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: 1357–1364. 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: 1386–1396. doi:10.1021/cs502011x.

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