1,1'-Bis(diphenylphosphino)ferrocene

1,1'-Bis(diphenylphosphino)ferrocene


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
PubChem	635956
ChemSpider	21865114^Y
ChEBI	CHEBI:30743
Jmol-3D images	Image 1 Image 2
SMILES 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] c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1
InChI InChI=1S/2C17H14P.Fe/c21-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h21-14H;^Y Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N^Y InChI=1/2C17H14P.Fe/c21-3-9-15(10-4-1)18(17- -13-7-8-14-17)16-11-5-2-6-12-16;/h21-14H;/q2-1;+2 Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N InChI=1/2C17H14P.Fe/c21-3-9-15(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
Properties
Molecular formula	C₃₄H₂₈FeP₂
Molar mass	554.391
Melting point	181-183 °C
Hazards
R-phrases	R25
S-phrases	S28A S45
Main hazards	Toxic
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,1'-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is a substituted phosphine commonly used, as are other phosphines, as a ligand in organometallic chemistry. It contains a ferrocene moiety in its backbone, and is closely related to other bridged diphenylphosphines such as 1,1-bis(diphenylphosphino)methane (dppm) and 1,2-bis(diphenylphosphino)ethane (dppe).

Preparation

This compound is commercially available. It may be prepared by the lithiation of ferrocene with n-butyllithium in the presence of TMEDA, followed by reaction with chlorodiphenylphosphine:^[1]

Dppf readily forms complexes with various metals;^[2] the palladium derivative, (dppf)PdCl₂ is especially popular for palladium-catalyzed coupling reactions. It is easily prepared in the usual manner, by reaction of dppf with the acetonitrile or benzonitrile complexes of palladium dichloride:^[2]

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

^ Ian R. Butler (2010). "3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives". In J. Derek Woollins (Google Books excerpt). Inorganic Experiments. pp. 175–179. ISBN 9783527324729. http://books.google.com/books?id=IlL_qLqj_nUC&pg=PA173.
^ ^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.