Palladium-Catalyzed Cross Coupling
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- Add 4-iodoacetophenone (246 mg, 1 equivalent, 1 mmol), acrylic acid (100 μL, 1.5 equivalents, 1.5 mmol), sodium carbonate (Na2CO3, 318 mg, 3 equivalents, 3 mmol), PdCl2 (2 mg, 0.01 equivalents, 0.01 mmol), and water (5 mL, 0.2 M) to a round bottom flask (~ 20 mL) equipped with a magnetic stir bar.
- Heat the reaction to approximately 100 °C and stir until complete consumption of 4-iodoacetophenone (approximately 1 h).
- The reaction can be monitored by TLC.
- Cool the reaction mixture to room temperature after completion.
- Acidify the reaction mixture with 1 M aqueous HCl to ~ pH of 1.
- The pH of the reaction mixture can be checked with litmus paper.
- A solid should precipitate.
- Collect the solid via filtration.
- Purify the crude material by recrystallization using a 1:1 mixture of methanol/water.
Source: Vy M. Dong and Faben Cruz, Department of Chemistry, University of California, Irvine, CA
This experiment will demonstrate the concept of a pal…
Chapters in this video
0:04
Overview
0:51
Principles of Palladium-Catalyzed Cross-Coupling Reactions
2:52
Heck Coupling Reaction
3:52
Isolation and Purification of Heck Coupling Product
4:46
Applications
6:03
Summary
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