Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature
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- 2 February 2018
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 20 (3), 888-891
- https://doi.org/10.1021/acs.orglett.8b00023
Abstract
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.Funding Information
- Ministry of Education of the People's Republic of China
- Ministry of Science and Technology of the People's Republic of China (2017YFA0303500)
- National Natural Science Foundation of China (21325208, 21572212)
- Chinese Academy of Sciences
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