N-Allylation of imides with allyl alcohol catalyzed by Pd(OAc)
2-bis (phosphine) was investigated. When 1, 3, 5-triazine-2, 4, 6 (1H, 3H, 5H)-trione was used as a substrate, Pd (OAc)
2-dppb[dppb=1, 4-bis (diphenylphosphino) butane] was found to be the most efficient catalyst, and the reaction proceeded effectively in aromatic hydrocarbon solvents such as xylene or toluene at temperatures of 110∼140 °C. For example, 1, 3, 5-trially1-1, 3, 5-triazine-2, 4, 6(1H, 3H, 5H)-trione was obtained in a quantitative yield from a Pd (OAc)
2-dppb (0.1-0.3 mmol) catalyzed reaction of 1, 3, 5-triazine-2, 4, 6 (1H, 3H, 5H) -trione and allyl alcohol in o-xylene at 110 °C for 4 h. Similarly, various N-allyl imides were also synthesized in high yields from allyl alcohol and the corresponding N-unsubstituted imides, such as succinimide, phthalimide or hydantoin. Reactions of succinimide and various allylic alcohols were also examined, and a reaction mechanism including a π-allylpalladium complex formed by the oxidative addition of allyl alcohol was proposed.
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