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

Previous problemNext problem

3:13 minutes

Problem 59b

Textbook Question

Predict the products of the following reactions.
(b)

Verified step by step guidance

Identify the type of reaction: The reaction involves an aryl iodide and an organozinc reagent in the presence of a palladium catalyst, indicating a Negishi coupling reaction.

Understand the role of each component: The aryl iodide will act as the electrophile, while the organozinc compound will serve as the nucleophile. The palladium catalyst facilitates the coupling process.

Predict the coupling: In a Negishi coupling, the carbon atom bonded to the zinc in the organozinc reagent will form a new bond with the carbon atom bonded to the iodine in the aryl iodide.

Consider the regioselectivity: The reaction will proceed with the formation of a new carbon-carbon bond between the aryl group and the alkyl chain from the organozinc reagent, replacing the iodine atom.

Draw the product: The final product will be a compound where the aryl group is directly connected to the alkyl chain, with the iodine atom replaced by the alkyl group from the organozinc reagent.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Negishi Coupling

Negishi coupling is a cross-coupling reaction that forms carbon-carbon bonds between an organozinc compound and an organic halide, typically catalyzed by palladium. This reaction is highly useful in organic synthesis for constructing complex molecules. The presence of a palladium catalyst, such as Pd(PPh3)4, facilitates the transfer of the organic group from zinc to the halide, resulting in the formation of a new C-C bond.

Role of Palladium Catalyst

Palladium catalysts, like Pd(PPh3)4, play a crucial role in facilitating cross-coupling reactions by enabling the oxidative addition of the organic halide and the subsequent transmetalation with the organozinc reagent. The catalyst undergoes a series of redox cycles, allowing the coupling partners to form a new carbon-carbon bond efficiently. The choice of ligand, such as triphenylphosphine (PPh3), can influence the reaction's selectivity and rate.

Organozinc Reagents

Organozinc reagents, such as the ZnBr-alkene shown in the reaction, are nucleophilic species used in cross-coupling reactions like Negishi coupling. They are known for their relatively mild reactivity and compatibility with a wide range of functional groups. In the reaction, the organozinc compound donates its organic group to the palladium catalyst, which then couples it with the organic halide to form the desired product.

Watch next

Master Negishi Coupling Reaction with a bite sized video explanation from Johnny

Start learning