July 07, 2020, 07:35:25 PM
Forum Rules: Read This Before Posting


Topic: Looking for recommended Suzuki conditions  (Read 3488 times)

0 Members and 1 Guest are viewing this topic.

Offline zuriel

  • Full Member
  • ****
  • Posts: 107
  • Mole Snacks: +2/-1
Looking for recommended Suzuki conditions
« on: April 12, 2017, 07:22:45 AM »
Hi everyone,

So, long story short - I haven't got much of this material (see attached structure) and I'm looking to try a Suzuki on it. Not really critical if it doesn't work but I'd like to see if anyone here has any recommended conditions.

The indolocarbazole itself is quite insoluble so I'm thinking of using perhaps DMF with tetrakis as the catalyst and caesium carbonate as the base.

Any help/advice is greatly appreciated.

Offline organic92

  • New Member
  • **
  • Posts: 5
  • Mole Snacks: +0/-0
Re: Looking for recommended Suzuki conditions
« Reply #1 on: April 15, 2017, 06:46:05 PM »
Try with K3PO4 maybe you can use dioxane, ether or Dioxane:H2O

Offline wildfyr

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 1503
  • Mole Snacks: +158/-9
Re: Looking for recommended Suzuki conditions
« Reply #2 on: April 15, 2017, 07:23:10 PM »
Usually DMSO is a little better at solubilizing big piles of aryl

Offline phth

  • Chemist
  • Full Member
  • *
  • Posts: 466
  • Mole Snacks: +35/-4
Re: Looking for recommended Suzuki conditions
« Reply #3 on: April 17, 2017, 02:30:31 AM »
PEG is the best cosolvent because it dissolves everything, and if palladium precipitates, it will form nanoparticles as active catalysts increasing the turnover of the reaction.

Offline wildfyr

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 1503
  • Mole Snacks: +158/-9
Re: Looking for recommended Suzuki conditions
« Reply #4 on: April 17, 2017, 10:52:49 AM »
@pth,
That is a brilliant contribution, but one word of caution: choose your molecular weight carefully. Some PEG MWs will like water, some will like organics. There is a weird game of trading you can play with workups in water/DCM/chloroform/ether depending on the MW. Just something to keep in mind if OP goes this (clever) route.

Offline zuriel

  • Full Member
  • ****
  • Posts: 107
  • Mole Snacks: +2/-1
Re: Looking for recommended Suzuki conditions
« Reply #5 on: April 18, 2017, 06:49:31 AM »
Thanks for the suggestions guys! I'll definitely have a look into either DMSO or (interestingly) PEG.

Offline zuriel

  • Full Member
  • ****
  • Posts: 107
  • Mole Snacks: +2/-1
Re: Looking for recommended Suzuki conditions
« Reply #6 on: April 18, 2017, 06:52:33 AM »
Try with K3PO4 maybe you can use dioxane, ether or Dioxane:H2O

What is the role of the tripotassium phosphate?

Offline prozen

  • New Member
  • **
  • Posts: 8
  • Mole Snacks: +0/-0
Re: Looking for recommended Suzuki conditions
« Reply #7 on: April 22, 2017, 10:40:19 AM »
Try with K3PO4 maybe you can use dioxane, ether or Dioxane:H2O

What is the role of the tripotassium phosphate?

K3PO4 is a base required to activate your boronic acid towards transmetallation via the boronate species. Alternatively, depending on which mechanism you believe, the base forms an oxopalladium intermediate that allows for transmetallation. It's a reasonably weak base and I've used it before (3-4 eq).

Offline prozen

  • New Member
  • **
  • Posts: 8
  • Mole Snacks: +0/-0
Re: Looking for recommended Suzuki conditions
« Reply #8 on: April 22, 2017, 10:41:01 AM »
Hi everyone,

So, long story short - I haven't got much of this material (see attached structure) and I'm looking to try a Suzuki on it. Not really critical if it doesn't work but I'd like to see if anyone here has any recommended conditions.

The indolocarbazole itself is quite insoluble so I'm thinking of using perhaps DMF with tetrakis as the catalyst and caesium carbonate as the base.

Any help/advice is greatly appreciated.

Out of interest, what was your synthesis for that compound? Are you following a paper?

Sponsored Links