Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis

Katsumi Maeda, Ryosuke Matsubara and Masahiko Hayashi*

*Department of Chemistry, Graduate School of Science, Kobe University, Kobe 657-8501, Japan, Email: mhayashikobe-u.ac.jp

K. Maeda, R. Matsubara, M. Hayashi, Org. Lett., 2021, 23, 1530-1534.

DOI: 10.1021/acs.orglett.0c04056

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Abstract

The use of a Pd/C-ethylene system enables a synthesis of anilines and indoles from cyclohexanones in the presence of NH₄OAc. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

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Key Words

anilines, indoles

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ID: J54-Y2021