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Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N‑(Acyloxy)­phthalimides at Room Temperature

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journal contribution
posted on 18.01.2018, 17:22 by Guang-Zu Wang, Rui Shang, Yao Fu
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.