The Stille cross-coupling reaction uses a palladium catalyst to couple an organohalide and an organostannane. The mechanism follows the expected oxidative addition-reductive elimination.
- Reagents: Catalytic Palladium (Pd(PPh3)4, Pd(dba)2, etc.)
- Reactant: Organohalide, Organostannane
- Product: Coupled Product
- Type of Reaction: C-C Cross-Coupling
Lab Tips
- Organostannanes are easy to work with as they are not sensitive to moisture or oxygen unlike other reactive organometallic reagents.
- Reaction conditions are compatible with carboxylic acid, amide, ester, nitro, ethers, amine, hydroxyl, ketone, and formyl groups.
- They are toxic however and it is difficult to remove traces of tin by-products from the reaction mixture.
- Oxidative homocoupling of the organostannane reagent is a possible side reaction.
Mechanism
Top Citations
Original Paper
Related Reactions
- Heck Reaction
- Hiyama Coupling
- Fukuyama Coupling
- Negishi Cross-Coupling
- Kumada Cross-Coupling
- Appel Reaction
- Suzuki Cross-Coupling
Related Compounds
- Organostannane
- Palladium Catalysts
