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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: dani on March 05, 2025, 09:01:17 AM

Title: Boronic acid for suzuki-myura coupling
Post by: dani on March 05, 2025, 09:01:17 AM

Hi, I found a  synthetic procedure for 3-aryl-coumarin in litterature (see image coumarin formation 1).
I would like to obtain the product in the image coumarin formation 2 through the similar procedure. I would like to introduce a boronic ester group to use the coumarin in a suzuki-miyura couplin with an aryl bromide. The question is, could the boronic ester inhibit the reaction? It is a lewis acid so it could be a catalyst for this reaction , but I am afraid that it could bound to the hydroxy group of the salicyl-aldehyde reagent inhibiting the reaction.
Thank you very much

Title: Re: Boronic acid for suzuki-myura coupling
Post by: rolnor on March 06, 2025, 03:22:53 AM

If the reaction on the top works, it seems probable that the bottom reaction should work. How do you plan to introduce the boronic substituent?

Title: Re: Boronic acid for suzuki-myura coupling
Post by: dani on March 06, 2025, 05:42:16 AM

Hi , thanks for your answer, I will buy the reagent, both boronic acid and pinacol boronic ester of phenilacetic acid are avalable.
so you think that my approach (coumarin formation 2 top image) could work and the final product could be used in a suzuki miyura coupling?

Title: Re: Boronic acid for suzuki-myura coupling
Post by: rolnor on March 15, 2025, 01:07:54 AM

Yes, what are you worried about could happen?

Title: Re: Boronic acid for suzuki-myura coupling
Post by: dani on March 18, 2025, 10:47:48 AM

I was worried about that my approach for cumarin synthesis (2 top reaction) with para-boronic pinacolester phenil acetic acid may not work