No.143
Synthesis of Polysubstituted Olefins
| A2174 | Acetophenone p-Toluenesulfonylhydrazone (1a) |
5g |
| P1813 | 3-Pentanone p-Toluenesulfonylhydrazone (1b) |
5g |
| C2295 | Cyclohexanone p-Toluenesulfonylhydrazone (1c) |
5g |
| C2296 | Cyclopentanone p-Toluenesulfonylhydrazone (1d) |
5g |
Barluenga et al. have reported the synthesis of polysubstituted olefins using N-tosylhydrazones 1. The reaction of 1 with an equivalent of aryl halide in the presence of a palladium catalyst and a base proceeds to give polysubstituted olefins. In this method, a stoichiometric amount of an organometallic reagent is not required, unlike the Kumada, Negishi, and Stille coupling reactions. Thus, broad future application of this method is expected.
References
N-Tosylhydrazones as reagents for cross-coupling reactions
J. Barluenga, P. Moriel, C. Valdés, F. Aznar, Angew. Chem. Int. Ed. 2007, 46, 5587.[DOI]
J. Barluenga, P. Moriel, C. Valdés, F. Aznar, Angew. Chem. Int. Ed. 2007, 46, 5587.[DOI]
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