Does the ester bond in my compound breaks If I proceeded a Sonogashira coupling reaction to react my compound (R-O-CO-Ar-Br) with the alkyne derivative?
The reaction condition I'm using:
Bis(triphenylphosphine)palladium(II); DME; TEA; CuI; 200 C; 24h
Thanks!!
Dear Abdulrahman Moursy Mahgoub, according to the attached reference (unfortunately I do not have the full text available) the ester groups should be stable under these conditions. I hope this helps.
I've done Sonogashira couplings with aromatic esters as you describe and they work fine.
I also done Sonogashira cross-coupling with aromatic ester and still stable
Ester will not breaks If you proceeded a Sonogashira coupling reaction to react my compound (R-O-CO-Ar-Br) with the alkyne derivative in an organic non-aqeous solvents.
You might have cleavage of the ester depending on the base you use, but most bases traditionally employed in Sonogashira couplings should be safe.
Dear Abdulrahman Mahgoub, the cleavage of the function ester happen depending on the type of solvent and the base used.
My advice for you us try to distil both the TEA and the DME.
Ester will be stabke and not breaks If you proceeded a Sonogashira coupling reaction
Dear A. Mahgoub, in general esters are stable. But to a quest, base hydrolysis of esters are reported to take place in aqueous medium. So, it is suggestible to perform the reaction using mild bases in organic solvents.
Abdulrahman,
As mentioned already, normally with the suggested base (Et3N) esters would be stable; however, the other reaction conditions could be problematic: 200 C, 24 h. Do you really need such harsh conditions for this reaction ?
Ester does not breaks in Sonogashira coupling reaction involving reaction of the halo compound (R-O-CO-Ar-Br) with the alkyne derivative under normal condition.
Ester will not break in sonogashira coupling reactions But i think no need of such hard condition for Sonogashira coupling reaction.
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