Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 9, Pages 3478-3483Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900396z
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- General Sekiyu Research Foundation
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The direct oxidative coupling of 2-amino- and 2-hydroxybenzoic acids with internal alkynes proceeds efficiently in the presence of a rhodium/copper catalyst system under air to afford the corresponding 8-substituted isocoumarin derivatives, some of which exhibit solid-state fluorescence. Depending on conditions, 4-ethenyl-carbazoles can be synthesized selectively from 2-(arylamino)benzoic acids. The oxidative coupling reactions of heteroarene carboxylic acids as well as aromatic diacids with an alkyne are also described.
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