1,1'-Bis(diphenylphosphino)ferrocene

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1,1'-Bis(diphenylphosphino)ferrocene
Dppfnew.png
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Identifiers
CAS number 12150-46-8
PubChem 635956
ChemSpider 21865114 YesY
ChEBI CHEBI:30743
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C34H28FeP2
Molar mass 554.391
Melting point 181-183 °C
Hazards
R-phrases R25
S-phrases S28A S45
Main hazards Toxic
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

1,1'-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorus compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines such as 1,2-bis(diphenylphosphino)ethane (dppe).

Preparation[edit]

This compound is commercially available. It may be prepared by treating dilithioferrocene with chlorodiphenylphosphine:[1]

Fe(C5H4Li)2 + 2 ClPPh2 → Fe(C5H4PPh2)2 + 2 LiCl

The dilithiation of ferrocene is easily achieved with n-butyllithium in the presence of TMEDA. Many related ligands can be made in this way. The Fe center is typically not involved in the behavior of the ligand.

Reactions[edit]

Dppf readily forms metal complexes.[2] The palladium derivative, (dppf)PdCl2, which is popular for palladium-catalyzed coupling reactions, is prepared by treating dppf with the acetonitrile or benzonitrile adducts of palladium dichloride:[2]

dppf + PdCl2(RCN)2 → (dppf)PdCl2 + 2 RCN (RCN = acetonitrile or benzonitrile)
Structure of the complex PtCl2(dppf).

See also[edit]

References[edit]

  1. ^ Ian R. Butler (2010). "3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives" (Google Books excerpt). In J. Derek Woollins. Inorganic Experiments. pp. 175–179. ISBN 978-3-527-32472-9. 
  2. ^ a b Nataro, Chip; Fosbenner, Stephanie M. (2009). "Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene". J. Chem. Ed. 86 (12): 1412. doi:10.1021/ed086p1412.