Cyrax (Hive Bee)
10-19-02 00:36
No 370041
      DPPF price? Organometalic reactions, do they suck?  Bookmark   

Check out p 8 of:

../rhodium/pdf /nickel-on-charcoal.pdf

There you can see the use of a compound called 1,1'-bis(diphenylphosphanyl)-ferrocene (DPPF) as a ligand in organometallic reactions.  I was intrigued by this, so I fetched the article about the aromatic amination by heterogeneous Ni°/C catalysis.

The authors states the following: "Given the importance of aryl amines in a variety of contexts (e.g. pharmaceuticals), a potentially scaleable heterogenous process which utilizes inexpensive chloride precursors and nickel rather than palladium may provide a welcomed complement to existing protocols."

Yeah right, I guess nickel is a pretty damned sure cheaper than palladium.  But what about the 1,1'-bis(diphenylphosphanyl)-ferrocene?
Looking at the molecular structure, I don't think this can be a cheap compound.

Can someone please look up how much this DPPF costs (say 5 grams)?  The reaction requires this specific ligand, they tried it with others - but it didn't work ...
(Hive Prodigy)
10-19-02 00:57
No 370050
      Hmm  Bookmark   

Fluka lists 1,1'-bis(diphenylphosphino)ferrocene (is this the same as your compound?) for $26/1g or 145$/10g.

Aldrich has it for $25/g or $139/10g

(Hive Bee)
10-19-02 01:19
No 370064
      Yes, it's the same compound.  Bookmark   

Yes, it's the same compound.

Whow, that's rather expensive.
In an example they use 50.5 mg Ni/C and 10.7 mg DPPF for 104.2 mg 4-chlorobenzonitrile.  So, when you want to do a 100 g reaction, it will cost like $140 ... taken into account the ligand alone.  Furthermore, the reaction requires n-BuLi  ==> strictly dry conditions and an argon atmosphere.  I wouldn't want to use that reaction at an industrial scale ...

Thanks for looking this up, PrimoPyro.