Octet / Reactions
Sonogashira Coupling
Sonogashira Coupling (Coupling.) Converts c1ccccc1Br to c1ccccc1C#CC using Terminal alkyne, Pd catalyst, CuI (co-catalyst), amine base.
Coupling
Reaction details
Name
Sonogashira Coupling
Type
Coupling
Starting Material
c1ccccc1Br
Product
c1ccccc1C#CC
Reagents
Terminal alkyne
Pd catalyst
CuI (co-catalyst)
amine base
Mechanism
- Smiles
c1ccccc1Br
- Description
Aryl halide
- Smiles
C#CC
- Description
Terminal alkyne (propyne)
- Smiles
c1ccccc1C#CC
- Description
Aryl-substituted alkyne
Tips
Aryl halide + Terminal alkyne → Aryl alkyne
Cu activates alkyne for transmetalation
Room temperature, mild conditions
Used heavily in pharmaceutical synthesis
Related Reactions
suzuki-coupling
heck-reaction
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