Octet / Reactions
Stille Coupling
Stille Coupling (Coupling.) Converts c1ccccc1Br to c1ccccc1C=C using R-SnBu₃ (organostannane), Pd catalyst.
Coupling
Reaction details
Name
Stille Coupling
Type
Coupling
Starting Material
c1ccccc1Br
Product
c1ccccc1C=C
Reagents
R-SnBu₃ (organostannane)
Pd catalyst
Mechanism
- Smiles
c1ccccc1Br
- Description
Aryl halide
- Smiles
[Sn](CCCC)(CCCC)(CCCC)C=C
- Description
Vinyl tributylstannane
- Smiles
c1ccccc1C=C
- Description
Styrene
Tips
Very functional group tolerant
Stannanes are stable but TOXIC (Sn)
Being replaced by Suzuki in many applications
Still used for complex molecule synthesis
Related Reactions
suzuki-coupling
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