I am planning a synthesis using a Stille cross-coupling reaction and for this I need to prepare a Ar-Sn(Bu)3organic compound.
Does any one has experience in the purification and stability of Ar-Sn(Bu)3organic compounds?
I found in the literature that most of the purifications of the Ar-Sn(Bu)3 compounds are carried out by vacuum distillation (using really low pressures) and a few examples using alumina column chromatography, does anyone have experience with these purifications and could give me some advice?
Many thanks for your help
Best regards,
Vicente
As Craig said, it will be fine by chromatography. For the separation from SnBu3Cl, 10 wt% K2CO3-silica gel is good. See: Chem. Commun. 2010, 46, 6335.
HI Vicente. Arylstannanes are perfectly fine by SiO2 chromatography in my experience, and are very non-polar - typically columned in petrol or
As Craig said, it will be fine by chromatography. For the separation from SnBu3Cl, 10 wt% K2CO3-silica gel is good. See: Chem. Commun. 2010, 46, 6335.
Yes, forgot to add that K2CO3 tip that Kohei mentioned.
For reference, that is excellent for removing Bu3Sn-halides, but not for Bu3Sn-H.
I purified butylstannylated compound by column chromatography on silica gel but I packed the column first with 80% petroleum ether and 20% triethyl amine and after adding the material to the column I used 95% petroleum ether and 5% triethyl amine as an eluent and I got my product pure and stable.
Silica gel chromatography works typically fine for me, unless your arylstannane is very apolar which makes it difficult to separate from starting distannane. Also, washing with 1M aq KF will remove a good part of tin salts and make the chromatographic purification easier.
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