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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: Parathormon on December 28, 2021, 01:32:27 PM

Title: Suzuki Coupling question
Post by: Parathormon on December 28, 2021, 01:32:27 PM

Hi everyone,

I have a question about Suzuki coupling - I am going to couple halo-compound with p-iodophenylboronic acid, and, there is a problem because iodophenylboronic acid has iodine atom which can couple with other molecule of p-iodophenylboronic acid and make polymers; also my product of reaction can be multicoupled on iodine of iodophenyl group attached…

Is there any method to prevent this?

Title: Re: Suzuki Coupling question
Post by: rolnor on December 28, 2021, 04:21:26 PM

You can use excess 1,4-diiodobenzene and a arylboronic acid, a Grignard+Fe salts  or a organotin+Pd (Stille). I think its difficult to use a iodo boronic acid. I have seen tetramethyltin coupling this way but larger alkyltins are probably slow.

This reaction could be an option: https://en.m.wikipedia.org/wiki/Negishi_coupling

Title: Re: Suzuki Coupling question
Post by: phth on January 02, 2022, 08:41:49 PM

the solution to pollution is dilution?

Title: Re: Suzuki Coupling question
Post by: rolnor on January 03, 2022, 02:18:35 AM

The iodophenylboronic acid does not change by dilution?

Title: Re: Suzuki Coupling question
Post by: BobfromNC on January 25, 2022, 04:05:23 PM

You can use fluoro and chloro boronic acids, but bromo and iodo do not work well, unless you want polymers.