Chemical Forums

Please login or register.

Login with username, password and session length

Sponsored links

Pages: [1]   Go Down

Author Topic: Removing Tin products in Stille coupling  (Read 1471 times)

0 Members and 1 Guest are viewing this topic.

vikram

  • Regular Member
  • ***
  • Mole Snacks: +1/-0
  • Offline Offline
  • Posts: 36
Removing Tin products in Stille coupling
« on: September 23, 2018, 01:39:16 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.
Logged

wildfyr

  • Global Moderator
  • Sr. Member
  • ***
  • Mole Snacks: +119/-9
  • Offline Offline
  • Posts: 1058
Re: Removing Tin products in Stille coupling
« Reply #1 on: September 23, 2018, 02:58:06 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
Logged

phth

  • Chemist
  • Full Member
  • *
  • Mole Snacks: +32/-4
  • Offline Offline
  • Posts: 416
Re: Removing Tin products in Stille coupling
« Reply #2 on: September 23, 2018, 08:46:12 PM »

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)
Logged

vikram

  • Regular Member
  • ***
  • Mole Snacks: +1/-0
  • Offline Offline
  • Posts: 36
Re: Removing Tin products in Stille coupling
« Reply #3 on: September 24, 2018, 12:07:12 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?
Logged

vikram

  • Regular Member
  • ***
  • Mole Snacks: +1/-0
  • Offline Offline
  • Posts: 36
Re: Removing Tin products in Stille coupling
« Reply #4 on: September 24, 2018, 12:09:18 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?
Logged

wildfyr

  • Global Moderator
  • Sr. Member
  • ***
  • Mole Snacks: +119/-9
  • Offline Offline
  • Posts: 1058
Re: Removing Tin products in Stille coupling
« Reply #5 on: December 05, 2018, 05:14:58 AM »

Sorry for the late response, missed it. yes that is what I meant.
Logged

rolnor

  • Full Member
  • ****
  • Mole Snacks: +34/-3
  • Offline Offline
  • Posts: 429
Re: Removing Tin products in Stille coupling
« Reply #6 on: December 05, 2018, 07:58:13 AM »

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.
Logged

clarkstill

  • Chemist
  • Full Member
  • *
  • Mole Snacks: +66/-4
  • Offline Offline
  • Posts: 371
Re: Removing Tin products in Stille coupling
« Reply #7 on: December 05, 2018, 09:17:18 PM »

Run your column in 10% K2CO3 in silica:

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

Works like a dream
Logged

vikram

  • Regular Member
  • ***
  • Mole Snacks: +1/-0
  • Offline Offline
  • Posts: 36
Re: Removing Tin products in Stille coupling
« Reply #8 on: December 05, 2018, 10:47:28 PM »

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)
Logged

zarhym

  • Regular Member
  • ***
  • Mole Snacks: +9/-1
  • Offline Offline
  • Gender: Male
  • Posts: 87
    • Linkedin
Re: Removing Tin products in Stille coupling
« Reply #9 on: December 07, 2018, 08:46:59 PM »

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.
Logged
Pages: [1]   Go Up
 

Mitch Andre Garcia's Chemical Forums 2003-Present.

Page created in 0.07 seconds with 25 queries.