The Vespiary

The Hive => Chemicals & Equipment => Topic started by: Cyrax on October 19, 2002, 12:36:00 AM

Title: DPPF price? Organometalic reactions, do they suck?
Post by: Cyrax on October 19, 2002, 12:36:00 AM

Check out p 8 of:

https://www.thevespiary.org/rhodium/Rhodium/pdf/nickel-on-charcoal.pdf (https://www.thevespiary.org/rhodium/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 ...

Title: Hmm
Post by: PrimoPyro on October 19, 2002, 12:57:00 AM

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

PrimoPyro

Title: Yes, it's the same compound.
Post by: Cyrax on October 19, 2002, 01:19:00 AM

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.