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Reaction id: 0402011003_05, verified by Personal Chemistry ©
Chemical 1c
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Chemical 2c
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Herrmann's ...
DBU
Mo(CO)6
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THF
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Product 3d
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Yield: 92% Time: 900s Temperature: 150 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 104-92-7 |
187.041 |
1.494 |
0.400 |
50.078 µl |
| 100-46-9 |
107.156 |
0.981 |
1.200 |
131.078 µl |
| Mo(CO)6 |
264.000 |
1.000 |
0.400 |
105.600 mg |
| DBU |
152.241 |
1.018 |
1.200 |
179.459 µl |
| Herrmann's catalyst |
937.618 |
1.000 |
0.020 |
18.752 mg |
| THF |
72.107 |
0.889 |
12.329 |
1000.000 µl |
| Product 1 |
241.290 |
1.000 |
0.000 |
0.000 µl |
Keywords
Catalysis, Catalytic, Catalyzed, Metal, Substitution, Aminocarbonylation
Comments
Synthesis: In this palladium-catalysed gas-free aminocarbonylation of aryl bromides and iodides the commercially available molybdenum hexacarbonyl served as a convenient and solid carbon monoxide source under air. Different solvents, bases and Pd-precatalysts were tested. The best conditions were obtained using DBU as a base and THF as solvent which made it possible to get even sluggish anilines, hindered tert-butylamine and free amino acids to react.
All reactants were mixed in a process vial which was immediately capped and irradiated with microwaves. The carbon monoxide release starts immediately on the addition of DBU.
Work-up and purification: After complete conversion and cooling, the reaction mixture was filtered through a short celite pad and the solvent, excess DBU and, if possible, excess amine were removed under reduced pressure. The residue was purified by silica gel flash chromatography (0-1% MeOH in CHCl3) to give the product as a white solid in 92% yield (>95% purity, GC/MS or 1H NMR).
Analysis and characterisation: 1H NMR, 13C NMR, GC/MS.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Wannberg, J.; Larhed, M. J. Org. Chem. 2003, 68, 5750-5753
Analysis
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