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Which conditions to do Suzuki coupling on a 3-aminoalkyl-6-chloropyridazine and 4-cyanophenylboronic acid. Tried Na2CO3,Pd(dppf)2 in DME/H2O, K2CO3, Sphos/Pd(AcO)2 in DMF and Na2CO3 Pd(Ph3)4 in dioxane/h2o but cannot get higher than 70% yield.
Accepted Answer
Optimizing Suzuki coupling conditions can be tricky! Here are some tips specific to your case:
1. Base: You've tried Na2CO3 and K2CO3. For challenging couplings, consider stronger bases like K3PO4 or Cs2CO3.
2. Solvent: DME/H2O and dioxane/H2O are good choices. DMF can sometimes cause side reactions, so if you're getting significant byproducts, try switching solvents.
3. Catalyst: Pd(dppf)2 and Pd(Ph3)4 are both classic choices, but exploring different ligands like SPhos can impact reactivity. Consider trying Buchwald-type catalysts like Pd(OAc)2 with XPhos.
4. Temperature: Try slowly increasing the reaction temperature. It might help overcome kinetic limitations.
5. Reactant Ratio: Ensure a slight excess of the boronic acid to drive the reaction forward.
6. Deaeration: Degassing the reaction mixture with nitrogen can reduce unwanted side reactions.
7. Purification: If you're struggling with purification, try using flash chromatography or recrystallization to isolate the desired product.
Let me know if you'd like me to suggest specific experimental conditions!
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