1,1'-Bis(diphenylphosphino)ferrocene
| 1,1'-Bis(diphenylphosphino)ferrocene | |
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1,1'- bis( diphenylphosphanyl) ferrocene |
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Other names
1,1'- Bis( diphenylphosphino) ferrocene, 1,1'- Ferrocenediyl- bis(diphenylphosphine), Dppf, 1,1'- Ferrocenebis (diphenylphosphine) |
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| Identifiers | |
| CAS number | 12150-46-8 |
| PubChem | 635956 |
| ChemSpider | 21865114  |
| ChEBI | CHEBI:30743 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C34H28FeP2 |
| Molar mass | 554.391 |
| Melting point |
181-183 °C |
| Hazards | |
| R-phrases | R25 |
| S-phrases | S28A S45 |
| Main hazards | Toxic |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
1,1'-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorous compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines 1,2-bis(diphenylphosphino)ethane (dppe).
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[edit] Preparation
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.
[edit] Reactions
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)
[edit] See also
- Diphosphines
- borrowing hydrogen catalysis
[edit] References
- ^ 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.
- ^ 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.
