Journal
ORGANIC LETTERS
Volume 20, Issue 3, Pages 888-891Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00023
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Funding
- NSFC [21325208, 21572212]
- MOST [2017YFA0303500]
- FRFCU
- PCSIRT
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It is reported that Pd(PPh3)(2)Cl-2 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 alpha-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 beta-hydride elimination of alkyl palladium intermediates.
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