Textbook Question
Suggest a mechanism for the reaction shown in Figure 16.30 using IZnCH₂I as the cyclopropanating reagent.
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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 23b
Predict the product of the following Negishi coupling reactions.
(b) 
Verified step by step guidance1
Identify the organolithium reagent: The starting material is an organolithium compound, specifically isopropyllithium, which is a strong nucleophile and base.
Convert the organolithium to an organozinc reagent: The first step involves the reaction of isopropyllithium with ZnCl2 in THF to form the corresponding organozinc compound, isopropylzinc chloride.
Recognize the role of the palladium catalyst: The Pd(PPh3)4 is a common catalyst used in Negishi coupling reactions, facilitating the cross-coupling between the organozinc reagent and the organic halide.
Identify the organic halide: The organic halide in this reaction is a bromocyclopentane with a fluorine substituent, which will undergo coupling with the organozinc reagent.
Predict the product: The Negishi coupling will result in the formation of a new carbon-carbon bond between the isopropyl group from the organozinc reagent and the carbon atom of the cyclopentane ring that was bonded to the bromine, yielding the coupled product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Negishi Coupling Reaction
Negishi coupling is a palladium-catalyzed cross-coupling reaction that forms carbon-carbon bonds between organozinc compounds and organic halides. It is widely used in organic synthesis to construct complex molecules. The reaction typically involves a transition metal catalyst, such as palladium, and proceeds through oxidative addition, transmetalation, and reductive elimination steps.
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Negishi Coupling Reaction
Transmetalation
Transmetalation is a key step in many cross-coupling reactions, including Negishi coupling, where an organometallic compound transfers its organic group to a metal catalyst. In this reaction, the organozinc species formed from the reaction of lithium reagent with ZnCl2 transfers its organic group to the palladium catalyst, facilitating the formation of the carbon-carbon bond with the organic halide.
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Palladium Catalysis
Palladium catalysis is crucial in facilitating cross-coupling reactions like Negishi coupling. Palladium complexes, such as Pd(PPh3)4, are used to activate organic halides through oxidative addition, allowing the subsequent transmetalation and reductive elimination steps to occur. This catalysis enables the formation of new carbon-carbon bonds efficiently and selectively, making it a powerful tool in organic synthesis.
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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 Stille coupling reactions.
(a)
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)
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Textbook Question
To determine the stereochemistry of curacin A by synthesis, it would have been necessary to prepare all stereoisomers of the C₁₇―C₂₀ cyclopropane fragment. How would the reaction in Figure 16.30 be modified to produce the other stereoisomers shown here?
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Textbook Question
Predict the product of the following Negishi coupling reactions.
(a)
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