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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: vikram on September 23, 2018, 07:39:16 AM

Title: Removing Tin products in Stille coupling
Post by: vikram on September 23, 2018, 07:39:16 AM: Do anyone have better idea to remove tin products in stille coupling?I have tried celite filtration and aqueous workup,however its not very efficient >:(

Its like a tar which is problematic during column chromatography.
Title: Re: Removing Tin products in Stille coupling
Post by: wildfyr on September 23, 2018, 08:58:06 AM: Have you tried just putting it through a plug of silica instead of running a full column? This is a good way to get rid of salts
Title: Re: Removing Tin products in Stille coupling
Post by: phth on September 24, 2018, 02:46:12 AM: Quote from: wildfyr on September 23, 2018, 08:58:06 AM
Have you tried just putting it through a plug of silica instead of running a full column? This is a good way to get rid of salts

Filter thru celite +Na/K•F(s)
Title: Re: Removing Tin products in Stille coupling
Post by: vikram on September 24, 2018, 06:07:12 AM: Quote from: wildfyr on September 23, 2018, 08:58:06 AM
Have you tried just putting it through a plug of silica instead of running a full column? This is a good way to get rid of salts

@wildfyr you mean to say using Silica as a filtration setup and then again running a full column?
Title: Re: Removing Tin products in Stille coupling
Post by: vikram on September 24, 2018, 06:09:18 AM: Quote from: phth on September 24, 2018, 02:46:12 AM

Filter thru celite +Na/K•F(s)

Can you please elaborate the method?

I am using CsF during the reaction. So Is KF/NaF needed?
Title: Re: Removing Tin products in Stille coupling
Post by: wildfyr on December 05, 2018, 11:14:58 AM: Sorry for the late response, missed it. yes that is what I meant.
Title: Re: Removing Tin products in Stille coupling
Post by: rolnor on December 05, 2018, 01:58:13 PM: If product is reasonable polar you can dissolve mixture in acetonitrile and wash with hexane to remove tin-organic.
If lipophilic you can dissolve in solvent and wash with KF och NaF-water solution.
Title: Re: Removing Tin products in Stille coupling
Post by: clarkstill on December 06, 2018, 03:17:18 AM: Run your column in 10% K2CO3 in silica:

https://pubs.rsc.org/en/content/articlepdf/2010/cc/c0cc01328e?page=search

Works like a dream
Title: Re: Removing Tin products in Stille coupling
Post by: vikram on December 06, 2018, 04:47:28 AM: Quote from: clarkstill on December 06, 2018, 03:17:18 AM
Run your column in 10% K2CO3 in silica:

https://pubs.rsc.org/en/content/articlepdf/2010/cc/c0cc01328e?page=search

Works like a dream

Thanks clarkstill. Its really great! Then during workup if I prepare a elite bed with potassium carbonate, it would help to remove both tin and Pd together right?I meant to say the column would be little less messy:)

(I usually obtain tar like polymerized tin compound after the reaction)
Title: Re: Removing Tin products in Stille coupling
Post by: zarhym on December 08, 2018, 02:46:59 AM: I would search stille coupling in OPRD journal. The reactions in this journal is often done in industrial scale (kilogram at least). I would be surprised if they are still doing columns at that scale.