Synthesis of Indoles via Domino Reactions of 2-Methoxytoluene and Nitriles.

J Org Chem

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.

Published: April 2023

2-Arylindoles are privileged structures widely present in biologically active molecules. New sustainable synthetic routes toward their synthesis are, therefore, in high demand. Herein, a mixed base-promoted benzylic C-H deprotonation of commercially available -anisoles, addition of the resulting anion to benzonitriles, and SAr to displace the methoxy group provide indoles. A diverse array of 2-arylindoles is prepared with good yields (>30 examples, yields up to 99%) without added transition metal catalysts.

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http://dx.doi.org/10.1021/acs.joc.2c02128DOI Listing

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