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.

• 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.

• Reagents: Catalytic Palladium (Pd(PPh₃)₄, Pd(dba)₂, etc.)
• Reactant: Organohalide, Organostannane
• Product: Coupled Product
• Type of Reaction: C-C Cross-Coupling

Mechanism

Original Paper

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