A General Method for Acylation of Indoles at the 3-Position with Acyl Chlorides in the Presence of Dialkylaluminum Chloride

Tatsuo Okauchi*, Masaaki Itonaga, Toru Minami, Takashi Owa, Kyosuke Kitoh and Hiroshi Yoshino

*Department of Applied Chemistry, Kyushu Institute of Technology, 1-1, Sensuicho, Tobata, Kitakyushu, 804-8550, Japan, Email: okauchiche.kyutech.ac.jp

T. Okauchi, M. Itonaga, T. Minami, T. Owa, K. Kitoh, H. Yoshino, Org. Lett., 2000, 2, 1485-1487.

DOI: 10.1021/ol005841p

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Abstract

Indoles are selectively acylated at position 3 in high yields with a broad range of acyl chlorides in the presence of diethylaluminum chloride or dimethylaluminum chloride. The reaction proceeds in CH₂Cl₂ under mild conditions and is applicable to indoles bearing various functional groups without NH protection.

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Key Words

Friedel-Crafts Acylation, Indoles

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ID: J54-Y2000