I have previously done sonagashira coupling of aryl bromides, with Pd catalyst and CuI in triethylamine solvent at 70C. The reaction was clean with very good yield. I tried the same conditions for aryl chlorides and it is not working even with increased temperatures and time.
Any suggestions for the reactions conditions for sonagashira coupling of aryl chlorides?
I have also tried the below publication and it didn't work for me:
Article ChemInform Abstract: Rapid and Efficient Pd-Catalyzed Sonoga...
Aryl chloride are not the most suitable candidate for the sonogashira coupling due to the strenght of the C-Cl bond. there is something like this quite recent article 10.1039/C6RA25416K.
If is possible I suggeest to switch to a Br or far better a Iodine derivatives
Thanks Fabrizio for your answer. But, the Pd catalyst suggested in 10.1039/C6RA25416K is too specialized. Also, I find it hard to trust many of the synthetic methodology papers.
I could synthesize my final compound by modifying the synthetic route.
Yeah i see is really specific as catalyst but i think it is necessary to involve such bond in a sonogashira. I hope you will find a good alternative route
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