Access to Indole Derivatives from Diaryliodonium Salts and 2-Alkynylanilines.

J Org Chem

Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University & Engineering Research Center of Molecular Medicine, Ministry of Education , Xiamen 361021, China.

Published: May 2016

An efficient, environmentally friendly, and operationally simple procedure to 1,2-disubstituted indoles from 2-alkynylanilines and diaryliodonium salts has been developed. This reaction proceeds smoothly under metal-free conditions. The products obtained could be transferred into 3,3'-diindolylmethane with DMSO catalyzed by palladium. The isotopic label experiments indicated that the methylene group in 3,3'-diindolylmethane is derived from DMSO. The diverse indoles were obtained in up to 90% yield for 28 examples.

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Source
http://dx.doi.org/10.1021/acs.joc.6b00106DOI Listing

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