Domanda del libro di testo
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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TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
Capitolo 15, Problema 31b
Predict the product of the following Sonogashira coupling reactions.
(b) 
Guida verificata passo dopo passo1
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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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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02:54
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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02:16Heck Reaction Mechanism
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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Percorso guidato
1:38Polymer Stereochemistry Concept 1
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Predict the product of the following Sonogashira coupling reactions.
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