Can I do heck coupling reaction on a compound in salt form without turning it into a free base?
As for example doing Heck coupling on p-chloropyridiniumchlroide.
I don't want to turn my compound into a free base because it contains nitrogen atoms that causes Pd toxicity and inhibit the coupling reaction.
Dear Hedhili,
Which part of the question isn't clear for you?
Again: Can I proceed Heck coupling reaction on an organic compound-in the salt form-in a base-free conditions?
Dear Aaron,
Thank you. My question is based on a work published in tetrahedron letters. In this work they proceeded the Heck coupling in a base-free condition.
You can check it here: https://doi.org/10.1016/j.tetlet.2011.06.081
I hesitated to answer your question as I suspected you had some sort of paper in mind when asking. Unfortunately, I cannot access the full paper so I can't comment further. My guess is that you may need one equiv of base. You can try with and without if you have enough material. Also solubility of your starting material may play a factor as well. Good luck.
The base is necessary for the course reaction; but I see that the work was done free-base
Hi Abdulrahman Mahgoub, please find attached the Supplementary Information of the Tetrahedron Letters paper to give you some more detailed information. The authors use a number of substituted heterocycles as starting materials for the Heck coupling, but they are all neutral. However, they use DMF as solvent. Chances are that your p-chloropyridiniumchloride is soluble in DMF. So you should just give it a try and run a test reaction on a small scale. Good luck!
@Frank T. Edelmann
Thanks prof. Edelmann. Do you think it will be a good idea to proceed the reaction in 90%DMf: 10%H20?
Hi Abdulrahman Mahgoub, I don't know if addition of water is a good idea. Did you check if the p-chloropyridiniumchloride is soluble in DMF alone?
My compound isn't a pyridinium chloride. But very similar as it's heterocyclic and in salt form also.
Unfortunately, it's poorly soluble in DMSO.
Dear Abdulrahman Mahgoub, in the end it is probably best to just try it out experimentally.
You can not proceed Heck coupling reaction(C-C bond forming) on a compound in the salt form . The reaction should be under anhydrous condition using aprotic solvents like DMF or ether .
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