|
|  |
Reaction id: 0601011013_09, verified by Personal Chemistry ©
Cyclohexylacetylene
|
|
lodobenzene
|
Bu4NOAc
Pd precatalyst
|
 |
NMP
|
|
p9
|
Yield: 94% Time: 600s Temperature: 110 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 931-48-6 |
108.184 |
0.828 |
0.600 |
78.394 µl |
| 591-50-4 |
204.010 |
1.000 |
0.500 |
102.005 mg |
| Pd precatalyst |
299.433 |
1.000 |
0.005 |
1.497 µl |
| Bu4NOAc |
301.515 |
1.000 |
0.530 |
159.803 mg |
| NMP |
99.133 |
1.028 |
51.850 |
5000.000 µl |
| Product 1 |
184.282 |
1.000 |
0.000 |
0.000 µl |
Keywords
Acetylation, Arylation, Catalysis, Catalyzed, Metal, Sonogashira Coupling, C-C coupling
Comments
Synthesis: This method was developed as a copper and amine free variation on Sonogashira coupling. It was found to work better for electron deficient aryl halides than for electron rich ones. Iodides were more reactive than bromides. The precatalyst was formed by mixing 4-pyridine aldoxime and Na2PdCl4. The resulting substance was insoluble in water as well as in most organic solvents (some solubility was detected in DMF and DMSO). The authors propose a quasi-polymeric complex structure for it (see also Solodenko, W.; Schön, U.; Messinger, J.; Glinschert, A.; Kirschning, A. Synlett 2004, 10, 1699-1702).
Work-up and purification: After the reaction, the mixture was washed with water and then twice extracted with MTBE. The solvent of the combined extracts was evaporated and the product purified by column chromatography on Celite eluted with hexane.
Characterisation: By HPLC.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Schön, U.; Messinger, J.; Genrich, F.; Solodenko, W.; Kirschning, A. Poster presentation at Advancing Library design & Organic Synthesis, San Diego Feb 14-17th, 2005
Analysis
|
|
|
|
|
