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 31b
Predict the product of the following Sonogashira coupling reactions.
(b) 
Verified step by step guidance1
Identify the reactants involved in the Sonogashira coupling reaction. The reactants are an aryl or vinyl halide and a terminal alkyne. In this case, the vinyl bromide and the terminal alkyne with a furan ring are the reactants.
Recognize the role of the catalysts and reagents. The reaction uses a palladium catalyst (Pd(PPh3)4) and a copper(I) iodide co-catalyst (CuI) in the presence of a base (iPr2NH). These facilitate the coupling of the alkyne to the vinyl halide.
Understand the mechanism of the Sonogashira coupling. The palladium catalyst first undergoes oxidative addition with the vinyl bromide, forming a palladium-vinyl complex.
The terminal alkyne is deprotonated by the base, forming a copper-acetylide intermediate. This intermediate then undergoes transmetallation with the palladium-vinyl complex, transferring the alkyne to the palladium center.
Finally, reductive elimination occurs, coupling the alkyne to the vinyl group and regenerating the palladium catalyst. The product is a conjugated enyne with the furan ring attached to the alkyne.
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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 formation of carbon-carbon bonds between terminal alkynes and aryl or vinyl halides. This reaction typically requires a palladium catalyst and a copper co-catalyst, facilitating the coupling process under mild conditions. Understanding the mechanism and the role of the catalysts is crucial for predicting the products of the reaction.
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Sonogashira Coupling Reaction
Reaction Mechanism
The reaction mechanism of the Sonogashira coupling involves several key steps: oxidative addition of the aryl halide to the palladium catalyst, followed by the coordination of the alkyne, and finally, reductive elimination to form the coupled product. A clear grasp of these steps helps in predicting the structure of the final product and understanding how different substituents on the reactants can influence the outcome.
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Regioselectivity and Stereochemistry
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry involves the spatial arrangement of atoms in the product. In Sonogashira reactions, the nature of the substituents on the aryl halide and alkyne can significantly affect both regioselectivity and stereochemistry, impacting the final product's properties and reactivity.
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Related Practice
Textbook Question
Predict the product of the diorganocuprate cross-coupling reactions shown.
(b)
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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.]
1
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Textbook Question
Predict the product of the following Stille coupling reactions.
(a)
Textbook Question
Predict the product of the diorganocuprate cross-coupling reactions shown.
(a)
1
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Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(a)
1
views