Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

35. Transition Metals

Negishi Coupling Reaction

Organic Chemistry

35. Transition Metals

Negishi Coupling Reaction

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2:43 minutes

Problem 23a

Textbook Question

Predict the product of the following Negishi coupling reactions.
(a)

Verified step by step guidance

Identify the reactants involved in the Negishi coupling reaction. In this case, we have a bromobenzene derivative and an organozinc compound.

Understand the role of the catalyst and solvent. The reaction uses a palladium catalyst, Pd(PPh3)4, and is carried out in tetrahydrofuran (THF) at 0°C.

Recognize the mechanism of the Negishi coupling reaction. The palladium catalyst facilitates the formation of a carbon-carbon bond between the aryl halide and the organozinc reagent.

Predict the product by replacing the bromine atom on the aromatic ring with the alkyl group from the organozinc compound. This results in the formation of a new C-C bond.

Draw the structure of the product, which is a combination of the aromatic ring with the methoxy group and the alkyl chain from the organozinc reagent, now attached to the position where the bromine was originally located.

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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 cross-coupling reaction that forms carbon-carbon bonds between an organozinc compound and an organic halide, facilitated by a palladium catalyst. This reaction is highly useful in organic synthesis for constructing complex molecules. The presence of a palladium catalyst and a suitable solvent, such as THF, is crucial for the reaction's success.

Role of Palladium Catalyst

Palladium catalysts, such as Pd(PPh3)4, are essential in facilitating the Negishi coupling reaction. They enable the oxidative addition of the organic halide to the palladium, followed by the transmetalation with the organozinc reagent, and finally, reductive elimination to form the desired carbon-carbon bond. The catalyst's efficiency is influenced by its ligands and the reaction conditions.

Transmetalation Process

Transmetalation is a key step in the Negishi coupling where the organozinc reagent transfers its organic group to the palladium complex. This step is crucial for forming the new carbon-carbon bond. The organozinc compound's reactivity and the reaction conditions, such as temperature and solvent, play significant roles in the efficiency of this process.

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Predict the product of the following Negishi coupling reactions.(a)

Key Concepts

Negishi Coupling Reaction

Role of Palladium Catalyst

Transmetalation Process

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Predict the product of the following Negishi coupling reactions.
(a)