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Topic: About the base in Suzuki coupling  (Read 3607 times)

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Offline kamiyu

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About the base in Suzuki coupling
« on: February 12, 2014, 06:37:09 PM »
I learn that base is used to activate the boronic acids. Is this true?

There are just lots of bases that can be used in the Suzuki coupling, and what determines when to use which???

Offline zsinger

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Re: About the base in Suzuki coupling
« Reply #1 on: February 12, 2014, 06:41:28 PM »
I wrote my masters thesis on this one reaction alone.  If you are asking questions like that, your not ready to perform one.  If, however, you do decide to do it, research the literature, and use their desired base.  There are many to choose from.  Hope this helps, and by no means am I trying to degrade your knowledge, intuition, or anything like that.  Just a extremely complicated procedure to master.
          -Zack
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Offline kamiyu

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Re: About the base in Suzuki coupling
« Reply #2 on: February 12, 2014, 06:58:24 PM »
Zack, thanks for your reply.

But I think you did not understand my question. I personally have also performed many Suzuki coupling on different substrates. What I would like to ask is what is the effect of base on the Suzuki coupling?

For example, some use K2CO3 but some may use CsF. Any clue about the effect of base (I think mainly in terms of basicity and solubility in organic solvent) ??

Offline zsinger

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Re: About the base in Suzuki coupling
« Reply #3 on: February 12, 2014, 07:07:20 PM »
Gotcha….I personally prefer Na2CO3, but K2CO3,, NaOEt, NaT-But-Oxide etc. work as well.  I find that the sodium does not tend to give me tons of crap in the glassware as some of the others so.  I would guess this is due to salt solubility.
           -Zack
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline Benzene

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Re: About the base in Suzuki coupling
« Reply #4 on: February 12, 2014, 07:54:50 PM »
I have noticed that triflouroborate salts are used occasionally with alkyl boranes. would a base be necessary in the this sort of modified suzuki? it seems like there would be no need to displace the halide from the Pd, nor the need to activate the boron.

Also, I see many of these reaction with unique catalysts. Why are these needed when tetrakis is proven to work?

Also, just a general question about Palladium. it seems like there are always 4 lone pairs around the metal center. when palladium is in its (0) oxidation state, its valence its filled, why do these bonds form?


Offline PhDoc

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Re: About the base in Suzuki coupling
« Reply #5 on: February 13, 2014, 03:00:29 PM »
K2CO3 is most commonly used, however please see this abstract of references:

http://www.chem.harvard.edu/groups/myers/handouts/12_Suzuki.pdf
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