Palladium-Catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp³)-H Activation: Concise Synthesis of Indole Derivatives

Takeshi Nanjo, Chihiro Tsukano and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email: takemotopharm.kyoto-u.ac.jp

T. Nanjo, C. Tsukano, Y. Takemoto, Org. Lett., 2012, 14, 4270-4273.

DOI: 10.1021/ol302035j

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Abstract

A Pd-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp³)-H activation allows the construction of the indole skeleton. Slow addition of isocyanide is effective for reducing the amount of catalyst needed and Ad₂PBu is a good ligand for C(sp³)-H activation. The construction of the tetracyclic carbazole skeleton was also achieved by a Pd-catalyzed domino reaction incorporating alkyne insertion.

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Key Words

indoles

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ID: J54-Y2012-2690