Dear all,
I would like to ask if anyone has experience in substrates (ethynylbenzene-based compound and bromide-benzene-based compound) that do not react using standard reaction conditions (P(PPh3)2Cl2, CuI in Et3N, Et2NH, Et3N/THF), we observed poor conversion and mainly starting materials in the reaction mixture.
Could anyone suggest alternative reaction conditions for this complicated substrates?
Many thanks
Dear Bartłomiej,
Many thanks for you very helpful reaction conditions, I will try them for our reaction system.
Best regards
Vicente
Thanks to all of you for your help!
We could get the reaction to work using Pd2(dba)3 and PPh3 in Et3N at reflux
Best regards
Hi Vicente,
The conditions I used are before are Pd(OAc)2 as catalyst, DMF as solvent, TMEDA as ligand, AgTFA as additive and my substrates are 2-iodothiophenol and phenylacetylene. And I don't use any copper salts. Hope this can help you.
Dear V. M. Centelles,
Sonogashira Coupling Reaction with Pd2(tpp)2Cl2 works well, however from my experience TEA doesn't gives fruitful results. Hence my better suggestion is to try with inorganic bases like K2CO3 or Cs2CO3 in Toluene.
You just change the amine , use diisopropyl amine and use Pd(PPh3)4 or PEPPSI catalysts. Maintain the reaction in inert condition.
Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide.You can change the solvent & temperature condition.
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