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Synfacts 2009(8): 0846-0846  
DOI: 10.1055/s-0029-1217452
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Dioxygen as Oxidant for the Synthesis of Indoles by Pd-Catalyzed C-H Activation

Contributor(s): Victor Snieckus, Emilie David
Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y. Cui, N. Jiao*
Peking University, Beijing and State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. of China
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Publikationsdatum:
23. Juli 2009 (online)

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Significance

Jiao and co-workers reported the synthesis of indoles from anilines and alkynes by a C-H activation process catalyzed by Pd(OAc)2 which uses dioxygen as the oxidant in the catalytic cycle. The best results were obtained when using a mixture of DMA and pivaloic acid (PivOH) as the solvent. The scope of the reaction was well studied. Thus, both EWGs and EDGs in the starting anilines were well tolerated whereas only electron-deficient alkynes afforded the corresponding indoles in modest to good yields. In addition, N-monosubstituted anilines participated efficiently in the reaction.