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Reaction id: 0501011045_01, verified by Personal Chemistry ©
a
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(R)-3a
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(Ph3P)4Pd
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THF
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product (1)
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Yield: 99% Time: 40s Temperature: 120 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| Substrate 1 |
191.956 |
1.000 |
1.200 |
230.347 µl |
| Substrate 2 |
506.124 |
1.000 |
0.198 |
100.000 mg |
| (Ph3P)4Pd |
1155.570 |
1.000 |
0.010 |
11.500 µl |
| THF |
72.107 |
0.889 |
61.645 |
5000.000 µl |
| Product 1 |
434.582 |
1.000 |
0.000 |
0.000 µl |
Keywords
Aryl-aryl coupling, Catalysis, Catalyzed, Metal, Negishi Coupling, C-C coupling
Comments
Synthesis: The zinc chloride reagent was prepared directly before this reaction by mixing ZnCl2 with aryllithium or arylmagnesium halide in THF under argon. To this solution the other reagents were added. This reaction was also carried out without microwave heating, and then gave 99% yield after 1 min of reflux. For other, less reactive substrates, the reaction took longer time and gave lower yields without microwaves.
Work-up and purification: After heating, the reaction mixture was diluted with wet diethyl ether and then concentrated. The product was isolated by flash chromatography (silica eluted with hexanes:ethyl acetate 50:1).
Characterisation: In the article, mp (181-184°) is cited. Spectral data were published elsewhere.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Krascsenicsova, K.; Walla, P.; Kasak, P.; Uray, G.; Kappe, C. O.; Putala, M. Chem Comm 2004, 2606-2607
Analysis
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