Naturalproductman’s Blog

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Triphenylphosphine (oxide) removal solved!

Posted by naturalproductman on October 25, 2014

You might remember an older post on something about the difficulty in removing triphenylphosphine or triphenylphosphine oxide removal. But first, how about a brief background: why would someone use triphenylphosphine in the first place? Well I can think of several reasons:

(1) Baylis-Hilman reaction

(2) Any metal cross coupling reaction using palladium tetrakis triphenylphosphine catalyst

(3) Mitsunobu reaction

So my particular problem was using the palladium tetrakis reagent to remove an Alloc protecting group.

You can see the details of the solution in page S-104 in supporting information file. But basically in a nutshell, instead of using tetrakis, I used Pd(DBA)2 and trimethylphosphine (PMe3) as the ligand, which evaporates at 38 degrees celsius.

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2 Responses to “Triphenylphosphine (oxide) removal solved!”

  1. Anonymous said

    I had a similar issue, also removing an Alloc group and ended up using Pd2(dba)3 and 1,4-bis(diphenylphosphino)butane as the ligand.

  2. naturalproductman said

    It did cross my mind to use that ligand and I even had it in hand, but I didn’t know if that diphenylphosphine part would actually change the polarity/solubility of the ligand in comparison with triphenylphosphine(?). Good to hear that that ligand has less problems with removal compared to triphenylphosphine, which gives us another alternative.

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