1,1'-Bis(diphenylphosphino)ferrocene
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| Names | |
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| IUPAC name
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 | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.167.773 |
PubChem CID
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| Properties | |
| C34H28FeP2 | |
| Molar mass | 554.391 |
| Melting point | 181 to 183 °C (358 to 361 °F; 454 to 456 K) |
| Hazards | |
| Main hazards | Toxic |
| R-phrases (outdated) | R25 |
| S-phrases (outdated) | S28A S45 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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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).
Contents
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)
See also[edit]
- Diphosphines
- borrowing hydrogen catalysis
References[edit]
- ^ Ian R. Butler (2010). "3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives". In J. Derek Woollins. Inorganic Experiments (Google Books excerpt). 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. Educ. 86 (12): 1412. doi:10.1021/ed086p1412.
