Reaction
- Catalyst for the Grignard coupling for regioand stereoselective monoalkylation and arylation of 1,1-dichloro-1-alkenes
- Synthetic pyrethriods: catalyst for the Negishi coupling of (2,2-dihaloethenyl)cyclopropanecarboxylates
Chemical Properties
yellow solid
Uses
Dichloro[bis(1,4-diphenylphosphino)butane]palladium(II) is used for the catalysis of styrene carbonylation, coupling of alkyl Grignard reagents with organic halides, selective monoalkylation of organic polyhalides, and modification of the dihalovinyl moiety of synthetic pyrethroids.
Preparation
Dichloro[1,4-bis(diphenylphosphino)butane]palladium(II) (1,4-Bis(diphenylphosphino)butane-palladium(II) chloride) can be prepared conveniently in situ by mixing the bidentate phosphine ligand and
(PhCN)2PdCl2 in either benzene or chloroform.
[1] The preparation of (dppb)PdCl2 is also possible through the
reaction of PdCl2 with dppb in acetone, a process that slowly forms the catalyst as a white precipitate which
can be isolated in 51% yield.
[2] Preparation of the hydrate complex is possible via the reaction of Na2[PdCl4]
with dppb in a mixture of CH2Cl2 and water.
reaction suitability
core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
References
1. Sugi, Y.; Bando, K.-I. CL 1976, 727.
2. Sanger, A. R. JCS(D) 1977, 1971.
