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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Meter on May 07, 2021, 06:08:57 AM

Title: Scope of Suzuki reagents?
Post by: Meter 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.

(https://i.imgur.com/ez8kRhX.png)

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?

Title: Re: Scope of Suzuki reagents?
Post by: rolnor 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.

Title: Re: Scope of Suzuki reagents?
Post by: Guitarmaniac86 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.

Title: Re: Scope of Suzuki reagents?
Post by: Meter on May 08, 2021, 04:12:54 AM

Thanks to both of you.

Title: Re: Scope of Suzuki reagents?
Post by: rolnor 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?