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

Buchwald-Hartwig Amination Reaction

Organic Chemistry

35. Transition Metals

Buchwald-Hartwig Amination Reaction

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2:59 minutes

Problem 25c

Textbook Question

Predict the product of the following reactions.
(c)

Verified step by step guidance

Identify the type of reaction: The presence of Pd(PPh3)4 and KOt-Bu suggests a Buchwald-Hartwig amination reaction, which is used to form carbon-nitrogen bonds.

Analyze the reactants: The starting materials include a chlorinated furan and a secondary amine. The furan ring is a five-membered aromatic ring containing an oxygen atom, and the amine is diethylamine.

Understand the mechanism: In Buchwald-Hartwig amination, the palladium catalyst facilitates the coupling of the aryl halide (chlorinated furan) with the amine. The base (KOt-Bu) deprotonates the amine, making it a better nucleophile.

Predict the product: The nitrogen atom of the deprotonated amine will attack the carbon atom bonded to the chlorine in the furan ring, resulting in the formation of a new C-N bond and the release of a chloride ion.

Consider the regioselectivity: Since the reaction involves a single chlorinated position on the furan, the amine will substitute at this position, leading to the formation of an N-aryl amine product with the furan ring intact.

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Key Concepts

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

Palladium-Catalyzed Cross-Coupling Reactions

Palladium-catalyzed cross-coupling reactions are a class of reactions that form carbon-carbon or carbon-heteroatom bonds using a palladium catalyst. In this reaction, Pd(PPh3)4 is used to facilitate the coupling between an aryl halide and an amine, leading to the formation of a new C-N bond. This process is crucial in organic synthesis for constructing complex molecules efficiently.

Buchwald-Hartwig Amination

The Buchwald-Hartwig amination is a specific type of palladium-catalyzed cross-coupling reaction where an amine is coupled with an aryl halide to form an aryl amine. This reaction typically requires a palladium catalyst, a ligand, and a base. In the given reaction, the amine is introduced to the chlorinated aromatic compound, resulting in the substitution of the chlorine atom with the amine group.

Role of Base in Cross-Coupling Reactions

Bases play a critical role in cross-coupling reactions by deprotonating the amine, which enhances its nucleophilicity, allowing it to effectively attack the aryl halide. In this reaction, KOt-Bu (potassium tert-butoxide) serves as the base, facilitating the formation of the C-N bond by activating the amine and stabilizing the palladium complex during the catalytic cycle.

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