Details

Item Description Structure
Catalog 8108 CAS 12150-46-8
Product Name 1,1'-Bis(diphenylphosphino)ferrocene
Other Name DPPF;1'-FERROCENEDIYL-BIS(DIPHENYLPHOSPHINE);1,1'-FERROCENEBIS(DIPHENYLPHOSPHINE);1,1'-bis(diphenyphosphino)ferrocene;1,1'-bis(diphenyphosphino)ferrocene(dppf);1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE, 97 %;1,1'-Bis(diphenylphosphino)ferrocene,99%DPPF
Purity 99% ee NA
Molecular Formula C34H28FeP2
Molecular Weight 554.39
Color and Form yellow to orange xtl.storage temp. 2-8C
Package 5g/10g and more Bulk Ordering Package
Solubility NA
Melting point 180C
Stability Stability: Stable. Incompatible with strong oxidizing agents.
Risk 25-36/37/38-20/21/22 Safety 22-24/25-45-28A-36-26 Hazard T,Xi,Xn
spectrometry Conforms to structure
HPLC Conforms to structure
Note Only for research purposes only
Technical Note

1,1'-Bis(diphenylphosphino)ferrocene Preparation Products And Raw materials
Preparation Products [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-->N,N'-Bis- (1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine-->1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex-->[1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II)
Raw materials Sodium hydroxide-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->n-Butyllithium-->N,N,N',N'-Tetramethylethylenediamine-->Ferrocene-->Dicyclopentadiene-->Ferrous chloride-->Chlorodiphenylphosphine

Technical Notes:
1. Ligand for Pd-catalyzed cross-coupling.
2. Useful ligand for Pd-catalyzed carbon-nitrogen and carbon-oxygen bond forming procedures.
3. Ligand for Ni-catalyzed amination of aryl chlorides.
4. Ligand for Pd-catalyzed conversion of aryl halides to aryl nitriles.
5. Ligand for Ni-catalyzed Suzuki reactions.
6. Ni-catalyzed hydroamination of 1,3-dienes.
7. Pd-catalyzed hydrocarbonation and hydroamination of 3,3-dihexylcyclopropene.
8. Pd-catalyzed -arylation of ,-unsaturated ketones.
9. Ligand for Ru-catalyzed reduction of nitriles to primary amines.
10. Ligand for Rh-catalyzed alkyne head-to-tail dimerization.
11. Ligand for Rh-catalyzed cross-coupling (Ref. 21).
12. Ligand for Rh-catalyzed olefin isomerization (Ref. 22).
13. Ligand for Ni or Rh-catalyzed borylation (Ref. 23, 24)
14. Ligand for regioselective Pd-catalyzed hydrophosphinylation of terminal alkynes to form branched alkenes.
References:
1. Pure Appl. Chem., 1980, 52, 669.
2. J. Am. Chem. Soc., 1989, 111, 314.
3. Palladium Reagents in Organic Synthesis (R.F. Heck), 1985, Chapter 6.
4. Comprehensive Organic Synthesis, 1991, Vol. 3, Chapter 2.
5. Acc. Chem. Res., 1998, 31, 852. (review)
6. J. Am. Chem. Soc., 1996, 118, 10333.
7. J. Am. Chem. Soc., 1996, 118, 13109.
8. Encyclopedia of Reagents for Organic Synthesis, 1995, Vol. 1, 518.
9. J. Am. Chem. Soc., 1997, 119, 6054.
10. Tetrahedron Lett., 2000, 41, 3271. (for ArCl)
11. Tetrahedron Lett., 1999, 40, 8193. (for ArBr)
12. Tetrahedron Lett., 1998, 54, 13079.
13. J. Org. Chem., 1995, 60, 1060.
14. J. Am. Chem. Soc., 2002, 124, 3669.
15. J. Org. Chem., 2003, 68, 2297.
16. Angew. Chem. Int. Ed., 2008, 47, 177.
17. Coordination Chem. Rev., 2007, 251, 2017. (review)
18. Chem. Eur. J., 2008, 14, 9491.
19. Dalton T., 2009, 36, 4926.
20. Anv. Synth. Catal., 2009, 9, 1371.
21. J. Org. Chem., 2009, 74, 2794.
22. J. Am. Chem. Soc., 2009, 131, 10822.
23. J. Am. Chem. Soc., 2012, 134, 115.
24. J. Am. Chem. Soc., 2010, 132, 1800.
25. J. Organomet. Chem., 2011, 1, 106.

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