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Total Synthesis of Indoles from Tricholoma Species via Bartoli/Heteroaryl Radical Methodologies

Adrian Dobbs

*Department of Chemistry, University of Exeter, Stocker Rd, Exeter, EX4 4QD, U.K., Email:

A. Dobbs, J. Org. Chem., 2001, 66, 638-641.

DOI: 10.1021/jo0057396


Treatment of o-bromonitrobenzenes with various vinyl Grignard reagents gives 7-bromoindoles in good yields, using the o-bromine atom to direct the cyclization. A subsequent reduction using a heteroaryl radical methodology gives 7-unsubstituted indoles in nearly quantitative yields.

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Key Words

Bartoli Indole Synthesis, Tributyltin Hydride, Dehalogenation, Indoles

ID: J42-Y2001-460