Textbook Question
Predict the product of the following Stille coupling reactions.
(b)
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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 31a
Predict the product of the following Sonogashira coupling reactions.
(a) 
Verified step by step guidance1
Identify the reactants involved in the Sonogashira coupling reaction. The reactants are a diiodobenzene derivative and an alkyne with a terminal hydrogen and an ester group (CO2Me).
Understand the role of the catalysts and base in the reaction. The reaction uses Pd(PPh3)4 as the palladium catalyst, CuI as the copper co-catalyst, and iPr2NH as the base. These components facilitate the coupling of the alkyne to the aryl iodide.
Recognize the mechanism of the Sonogashira coupling. The palladium catalyst first undergoes oxidative addition with the aryl iodide, forming a palladium-aryl complex. The copper co-catalyst activates the terminal alkyne, allowing it to form a copper-acetylide complex.
The palladium-aryl complex and the copper-acetylide complex then undergo transmetalation, where the acetylide group is transferred to the palladium, forming a palladium-acetylide complex.
Finally, reductive elimination occurs, where the palladium-acetylide complex forms a new carbon-carbon bond between the aryl group and the alkyne, resulting in the coupled product. Since there are two equivalents of the alkyne, both iodine groups on the benzene ring will be replaced by the alkyne, forming a bis-alkyne product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Sonogashira Coupling
The Sonogashira coupling is a cross-coupling reaction that involves the coupling of an aryl or vinyl halide with an alkyne in the presence of a palladium catalyst and a base. This reaction is widely used in organic synthesis to form carbon-carbon bonds, particularly in the construction of complex molecules and materials.
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Sonogashira Coupling Reaction
Palladium Catalysis
Palladium catalysis is a key component in many cross-coupling reactions, including the Sonogashira reaction. Palladium serves as a catalyst that facilitates the formation of the carbon-carbon bond by activating the halide and the alkyne, allowing for the efficient coupling of these two components under mild conditions.
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Reaction Mechanism
Understanding the reaction mechanism of the Sonogashira coupling is essential for predicting the products. The mechanism typically involves oxidative addition of the halide to the palladium, followed by alkyne coordination, and finally reductive elimination to form the coupled product. Analyzing the mechanism helps in anticipating the regioselectivity and stereochemistry of the final product.
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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)
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Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(b)
890
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Textbook Question
The trimethylsilyl (TMS) group, used as a protecting group for alcohols, can also be used a protecting group for terminal alkynes. Show how TMS-acetylene could be used to link together two aryl halides using the Sonogashira reaction. [Hint: Deprotection of the TMS-acetylene can be done using KF in H₂O.]
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Textbook Question
Predict the product of the following Stille coupling reactions.
(a)
997
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Textbook Question
Predict the product of the diorganocuprate cross-coupling reactions shown.
(a)
1008
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