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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 (free Supporting Information)


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


ID: J54-Y2000