1,1'-Bis(diphenylphosphino)ferrocene
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Preferred IUPAC name
(Ferrocene-1,1′-diyl)bis(diphenylphosphane) | |
Other names
1,1′-Bis(diphenylphosphino)ferrocene, 1,1′-ferrocenediylbis(diphenylphosphine), Dppf, 1,1′-ferrocenebis(diphenylphosphine), 1,1′-bis(diphenylphosphanyl)ferrocene
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Identifiers | |
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3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.167.773 |
EC Number |
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24075 | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Toxic |
GHS labelling: | |
Signal word
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Warning |
H302, H312, H315, H319, H332 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
what is ?) | (|
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[]
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[]
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] Substitution of the phenyl substituents in dppf leads to derivatives with modified donor-acceptor properties at the phosphorus atoms.[3]
- dppf + PdCl2(RCN)2 → (dppf)PdCl2 + 2 RCN (RCN = acetonitrile or benzonitrile)
See also[]
- Diphosphines
- borrowing hydrogen catalysis
References[]
- ^ Ian R. Butler (2010). "3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives". In J. Derek Woollins (ed.). 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.
- ^ Dey, Subhayan; Pietschnig, Rudolf (2021). "Chemistry of sterically demanding dppf-analogs". Coord. Chem. Rev. 437: 213850. doi:10.1016/j.ccr.2021.213850.
- Ferrocenes
- Tertiary phosphines
- Diphosphines