1,1'-Bis(diphenylphosphino)ferrocene

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).

1,1'-Bis(diphenylphosphino)ferrocene

Names
IUPAC name 1,1'-bis(diphenylphosphanyl) ferrocene
Other names 1,1'-Bis(diphenylphosphino) ferrocene, 1,1'-ferrocenediyl-bis(diphenylphosphine), Dppf, 1,1'- ferrocenebis (diphenylphosphine)
Identifiers
CAS Number	12150-46-8^Y[chemspider]
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:30743^Y
ChemSpider	21865114^Y
ECHA InfoCard	100.167.773
EC Number	640-119-0
Gmelin Reference	24075
PubChem CID	635956
UNII	L7Z23UWS3H^Y
CompTox Dashboard (EPA)	DTXSID20897535
InChI InChI=1S/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;^Y Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N^Y InChI=1/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17- -13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;/q2*-1;+2 Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N InChI=1/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;/rC34H28FeP2/c1-5-13-21(14-6-1)36(22-15-7-2-8-16-22)33-29-25-26-30(33)35(25,26,29,33)27-28(35)32(35)34(35,31(27)35)37(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20,25-32H Key: HPXNTHKXCYMIJL-KDKHWAOJAX
SMILES c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2]
Properties
Chemical formula	C34H28FeP2
Molar mass	554.391
Melting point	181 to 183 °C (358 to 361 °F; 454 to 456 K)
Hazards
Main hazards	Toxic
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	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).
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Infobox references

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]

dppf + PdCl₂(RCN)₂ → (dppf)PdCl₂ + 2 RCN (RCN = acetonitrile or benzonitrile)

Structure of the complex PtCl₂(dppf)

See also

• Diphosphines
• borrowing hydrogen catalysis

References

1. 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.
2. 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.