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  • Title: Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature.
    Author: Wang GZ, Shang R, Fu Y.
    Journal: Org Lett; 2018 Feb 02; 20(3):888-891. PubMed ID: 29345954.
    Abstract:
    It is reported that Pd(PPh3)2Cl2 in combination with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) under irradiation of blue LEDs efficiently catalyzes a decarboxylative Heck reaction of vinyl arenes and vinyl heteroarenes with aliphatic N-(acyloxy)phthalimides at room temperature. A broad scope of secondary, tertiary, and quaternary carboxylates, including α-amino acid derived esters, can be applied as amenable substrates with high stereoselectivity. The experimental observation was explained by excitation-state reactivity of the palladium complex under irradiation to induce single-electron transfer to activate N-(acyloxy)phthalimides, and to suppress undesired β-hydride elimination of alkyl palladium intermediates.
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