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
exeter.ac.uk
A. Dobbs, J. Org. Chem., 2001, 66, 638-641.
DOI: 10.1021/jo0057396
Abstract
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
