No.104
π-Allylpalladium Complex
| A1479 | Allylpalladium(II) Chloride Dimer (1) |
500mg |
The present reagent 1 performs quantitative allylation with a variety of nucleophiles1,2). For example, reaction with malonic acid esters leads to allyl substituted malonate derivatives. Furthermore, addition of reagent 1 and phosphine ligands to the reactions between nucleophiles and olefins leads to the formation of a new Pd-phosphine complex within the system which functions as a catalyst for the allylation reaction to proceed smoothly. In this case using asymmetric phosphine ligands such as L* allows asymmetric allylation reaction to occur3,4).
References
1) Reaction of π-allylpalladium chloride with nucleophiles
J. Tsuji, H. Takahashi, M. Morikawa, Tetrahedron Lett., 1965, 4387.
2) Organopalladium intermediates in organic synthesis
B. M. Trost, Tetrahedron, 33, 2615 (1977).
3) Chiral phosphinoaryldihydrooxazoles as ligands in asymmetric catalysis
P. von Matt, A. Pfaltz, Angew. Chem. Int. Ed. Engl., 32, 566 (1993).
4) Asymmetric catalytic allylation using palladium chiral phosphine complexes
P. R. Auburn, P. B. Mackenzie, B. Bosnich, J. Am. Chem. Soc., 107, 2033 (1985).
J. Tsuji, H. Takahashi, M. Morikawa, Tetrahedron Lett., 1965, 4387.
2) Organopalladium intermediates in organic synthesis
B. M. Trost, Tetrahedron, 33, 2615 (1977).
3) Chiral phosphinoaryldihydrooxazoles as ligands in asymmetric catalysis
P. von Matt, A. Pfaltz, Angew. Chem. Int. Ed. Engl., 32, 566 (1993).
4) Asymmetric catalytic allylation using palladium chiral phosphine complexes
P. R. Auburn, P. B. Mackenzie, B. Bosnich, J. Am. Chem. Soc., 107, 2033 (1985).
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