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Reaction id: 0601011009_20, verified by Personal Chemistry ©
Mo(CO)6
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2f
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3a
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[(t-Bu)3PH])BF4
DBU
Herrmann's ...
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1,4-Dioxane
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4e
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Yield: 96% Time: 900s Temperature: 140 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 13939-06-5 |
264.000 |
1.000 |
0.400 |
105.600 µl |
| 90-11-9 |
207.075 |
1.000 |
0.400 |
82.830 mg |
| Substrate 1 |
171.218 |
1.000 |
1.200 |
205.462 µl |
| Herrmann's catalyst |
937.618 |
1.000 |
0.020 |
18.752 mg |
| [(t-Bu)3PH])BF4 |
290.133 |
1.000 |
0.040 |
11.605 mg |
| DBU |
152.241 |
1.000 |
1.200 |
182.689 µl |
| 1,4-Dioxane |
88.106 |
1.034 |
11.736 |
1000.000 µl |
| Product 1 |
325.386 |
1.000 |
0.000 |
0.000 µl |
Keywords
Arylation, Carbonylation, Catalysis, Catalyzed, Metal, C-C coupling
Comments
Synthesis: This method was developed for both electronically and sterically diverse halides. It was shown to work well for a large number of iodides (at 110°C), and at a higher temperature (140°C) for bromides. As for the sulfonamide substrate, all primary compounds tried worked well, whereas secondary sulfonamide gave lower yields. The reaction was carried out under air.
Work-up and purification: After the reaction, the solvent was evaporated and the residue dissolved in dichloromethane. The product was then isolated by column chromatography first on silica eluted with 3:97->6:94 methanol:dichloromethane, then on aluminium oxide first eluted with 3:97->6:94 methanol:dichloromethane and then with 1:5:95 formic acid:methanol:dichloromethane.
Characterisation: By 1H NMR, 13C NMR, MS and elemental analysis.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Wu, X.; Rönn, R.; Gossas, T.; Larhed, M. J. Org. Chem. 2005, 70, 3094-3098
Analysis
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