4669. Herrmann-Beller Catalyst

Nomenclature

CAS number: 172418-32-5
Bis[μ-(acetato-κOO′)]bis[[2-[bis(2-methylphenyl)phosphino-κP]phenyl]methyl-κC]dipalladium stereoisomer; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); Herrmann's palladacycle.
C46H46O4P2Pd2; mol wt 937.64.
C 58.92%, H 4.94%, O 6.83%, P 6.61%, Pd 22.70%.

Description and references

Highly efficient palladacycle catalyst; exists in a monomer/dimer equilibrium in soln. Prepn: M. Beller et al., DE 4421753 (1995 to Hoechst); eidem, US 5831107 (1998 to Aventis); and catalytic applications: W. A. Herrmann et al., Angew. Chem. Int. Ed. 34, 1844 (1995); eidem, Chem. Eur. J. 3, 1357 (1997); W. A. Herrmann et al., J. Chem. Educ. 77, 92 (2000). EXAFS characterization: S. G. Fiddy et al., Chem. Commun. 2003, 2682. Catalysis mechanism in the Heck reaction: V. P. W. Bhm, W. A. Herrmann, Chem. Eur. J. 7, 4191 (2001). Review of catalytic applications: A. Speicher et al., J. Prakt. Chem. 341, 605-608 (1999).

Chemical structure

Properties

Yellow crystals from toluene/hexane or CH2Cl2/hexane, mp 229-231° (dec). Air stable; thermally stable; becomes catalytically active at ≈80°.

Use

Homogeneous catalyst in carbon-carbon bond forming reactions such as the Heck and Suzuki reactions.