Abstract
Product control of palladium-catalyzed aerobic oxidation of terminal olefins with electron-withdrawing groups can be achieved through modifying reaction conditions. When the oxidant, such as CuCl 2/O 2, benzoquinone/O 2 or O 2, was present in scCO 2, aerobic oxidation of terminal olefins goes smoothly. With enough MeOH and sufficient oxygen, acetalization preponderated over cyclotrimerization, while with little MeOH as co-solvent in scCO 2 or no MeOH in DMF and an appropriate pressure of O 2, cyclotrimerization of terminal olefins became the dominated reaction. When oxygen is absent and triethylamine was added into the reaction system, palladium-catalyzed C–N bond formation occurs to produce β-amino acid derivatives as the sole product.
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