June 20, 2021, 09:42:49 AM
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Topic: Scope of Suzuki reagents?  (Read 201 times)

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Offline Meter

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Scope of Suzuki reagents?
« on: May 07, 2021, 06:08:57 AM »
My textbook isn't exactly clear (or maybe I've missed something) on the scope of Suzuki reagents.  It seems that it works best for straight alkyl chains and aryl compounds? So,  I was wondering if something like the following is (theoretically) possible. Never mind practical concerns.



I guess the broader question is: Does it matter where on the compound the boron-group is placed - will the new C-C bond be coupled to the carbon that the boron-group is connected to?

Offline rolnor

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Re: Scope of Suzuki reagents?
« Reply #1 on: May 08, 2021, 03:05:48 AM »
Yes, you get the new bond where the boron is. I am not sure how stable the propenylboronic acid in the top scheme is.

Offline Guitarmaniac86

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Re: Scope of Suzuki reagents?
« Reply #2 on: May 08, 2021, 04:11:16 AM »
It does matter where the boronate is placed.

2-boronate pyridines and 2-fluoro-arylboronates are unstable.

The propenyl boronic acid/ester are "stable" as you can buy them, but they are prone to proto-deborylation. I am using it in my synthesis of [confidential drug molecule].

Further, Sp2 to Sp3Sp3couplings can be difficult to do because of proto-deborylation and the potential for hydride shifts/beta hydride eliminations on alkyl chains.
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Offline Meter

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Re: Scope of Suzuki reagents?
« Reply #3 on: May 08, 2021, 04:12:54 AM »
Thanks to both of you.

Offline rolnor

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Re: Scope of Suzuki reagents?
« Reply #4 on: May 08, 2021, 06:55:40 AM »
If the boronate is unstable it offcourse matters but if stable the new product will always have the new carbon-carbon bond in the same place as the boron-carbon bond in the boronic ester?

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