Predict the product of the following Stille coupling reactions.


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Verified step by step guidance

1. Identify the reactants involved in the Stille coupling reaction. Typically, this involves an organotin compound and an organic halide or pseudohalide.
2. Determine the nature of the organotin compound. It usually contains a tin atom bonded to an organic group, often an aryl or vinyl group.
3. Identify the organic halide or pseudohalide. This is often an aryl or vinyl halide, such as an aryl bromide or iodide.
4. Understand the mechanism: The Stille coupling involves the formation of a new carbon-carbon bond between the organic group of the organotin compound and the organic halide, facilitated by a palladium catalyst.
5. Predict the product: The new carbon-carbon bond forms between the carbon atom of the organotin compound and the carbon atom of the organic halide, resulting in a coupled organic product.

Key Concepts

Stille Coupling Reaction

The Stille coupling is a cross-coupling reaction that involves the reaction of an organostannane (tin-containing compound) with an organic halide in the presence of a palladium catalyst. This reaction is widely used in organic synthesis to form carbon-carbon bonds, allowing for the construction of complex molecules. Understanding the mechanism and conditions of this reaction is crucial for predicting the products formed.

Organostannanes

Organostannanes are organometallic compounds containing a carbon-tin bond, where tin is typically bonded to an alkyl or aryl group. They serve as nucleophiles in Stille coupling reactions, reacting with electrophilic partners such as organic halides. The stability and reactivity of these compounds are essential for successful coupling and product formation.

Palladium Catalysis

Palladium catalysis is a key component in many cross-coupling reactions, including the Stille reaction. Palladium serves as a catalyst that facilitates the formation of the carbon-carbon bond by activating the organic halide and promoting the coupling with the organostannane. Understanding the role of palladium and the reaction conditions, such as temperature and solvent, is vital for predicting the outcome of the reaction.