Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu­(I) as promoter and electron-rich ones by employing Pd­(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (−I, Br, and Cl) through th...

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Veröffentlicht in:Journal of organic chemistry 2016-04, Vol.81 (7), p.2794-2803
Hauptverfasser: Fu, Zhengjiang, Li, Zhaojie, Song, Yuanyuan, Yang, Ruchun, Liu, Yanzhu, Cai, Hu
Format: Artikel
Sprache:eng
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Zusammenfassung:Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu­(I) as promoter and electron-rich ones by employing Pd­(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (−I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe­(CN)6 under an oxygen atmosphere for the first time.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02873