Hey all!
Does any one have a trick to removing Pd(PPh3)4 from a cross-coupling reaction? In my case I did a Negishi coupling.
VinylMgCl was cooled to 0C and THF soln of ZnBr2 is added and stirred for 15 min. My vinyl iodide was dissolved in THF and 0.03 eq Pd(PPh3)4 was added. The homogeneous soln was added to the organozinc reagent. Let stir at RT 2.5 hr.
Quench with 3 aliquots of sat. ammonium chloride and then add 1/2 aliquot of hexanes. Extract aqueous. Wash aqueous with ammonium chloride, water, brine, dry. NMR looks great except the Pd(PPh3)4.
The problem is the complex is soluable in hexane/THF so celite is a no go. Any help would be great. I know removing these types of catalysts can be a pain. I am trying to do a reaction on scale and a column is just not practical.
Thank you in advance!
Cheers!