Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 19, Issue -, Pages 57-65Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.19.5
Keywords
decarboxylative cascade cyclization; iodide catalysis; metal-free photocatalysis; oxindole; phosphine catalysis
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A practical NaI/PPh3-catalyzed decarboxylative radical cascade cyclization of N-arylacrylamides with redox-active esters is reported in this study, which is mediated by visible light irradiation. A wide range of substrates derived from ubiquitous carboxylic acids, including alpha-amino acids, were successfully synthesized under this transition-metal-free and cost-effective synthetic method. The mechanistic experiments suggest a radical mechanism for this reaction.
A practical NaI/PPh3-catalyzed decarboxylative radical cascade cyclization of N-arylacrylamides with redox-active esters is de-scribed, which is mediated by visible light irradiation. A wide range of substrates bearing different substituents and derived from ubiquitous carboxylic acids, including alpha-amino acids, were synthesized and examined under this very mild, efficient, and cost effec-tive transition-metal-free synthetic method. These afforded various functionalized oxindoles featuring a C3 quaternary stereogenic center. Mechanistic experiments suggest a radical mechanism.
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