Textbook Question
Predict the product of the following Stille coupling reactions.
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Ch. 16 - Metals in Organic Chemistry
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 15, Problem 25a
Predict the product of the following Stille coupling reactions.
(a) 
Verified step by step guidance1
Identify the components of the Stille coupling reaction: an organotin compound and an organohalide. In this case, the organotin compound is the vinylstannane with a trimethylsilyl group, and the organohalide is the bromocyclopentene.
Recognize the catalyst and conditions: The reaction uses a palladium catalyst, Pd(PPh3)4, in toluene at 80°C. This is typical for Stille coupling reactions, which facilitate the formation of carbon-carbon bonds.
Understand the mechanism: The palladium catalyst will first undergo oxidative addition with the organohalide (bromocyclopentene), forming a palladium complex with the cyclopentene ring.
Transmetalation step: The organotin compound will transfer its organic group (vinyl group) to the palladium complex, replacing the bromine atom. This step is facilitated by the presence of the palladium catalyst.
Reductive elimination: The final step involves the reductive elimination of the palladium complex, forming a new carbon-carbon bond between the vinyl group and the cyclopentene ring, resulting in the coupled product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stille Coupling Reaction
The Stille coupling reaction is a palladium-catalyzed cross-coupling process that forms carbon-carbon bonds between an organotin compound and an organic halide. It is widely used in organic synthesis to construct complex molecules, often involving vinyl, aryl, or alkyl groups. The reaction typically requires a palladium catalyst, such as Pd(PPh3)4, and is performed under mild conditions, making it a versatile tool in synthetic chemistry.
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Stille Reaction
Organotin Compounds
Organotin compounds, such as the one depicted with a SnBu3 group, are key reagents in Stille coupling reactions. These compounds contain a tin atom bonded to carbon groups, which can transfer an organic moiety to a palladium catalyst. The organotin reagent in the reaction provides the carbon group that will couple with the organic halide, facilitating the formation of a new carbon-carbon bond.
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Palladium Catalysis
Palladium catalysis is crucial in facilitating the Stille coupling reaction. The palladium catalyst, often Pd(PPh3)4, activates the organic halide and the organotin compound, enabling the transmetalation and reductive elimination steps that form the new carbon-carbon bond. The catalyst's role is to lower the activation energy of the reaction, allowing it to proceed efficiently under relatively mild conditions, such as 80°C in toluene.
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Related Practice
Textbook Question
Work backward to an appropriate organozinc halide and organohalide to make the bonds indicated by the blue arrows. There may be two possibilities for each.
(b)
1
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Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(b)
1
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Textbook Question
Predict the product of the following Negishi coupling reactions.
(b)
2
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Textbook Question
Work backward to an appropriate organozinc halide and organohalide to make the bonds indicated by the blue arrows. There may be two possibilities for each.
(a)
1
views
Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(a)
1
views