Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 16, Pages 6291-6294Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo060911c
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The treatment of 2-fluorophenyl 2-iodophenylamines, ether, and thioether, easily prepared from commercially available products, with 3.3 equiv of t-BuLi and further reaction with selected electrophiles gives rise to functionalized carbazole, dibenzofuran, and dibenzothiophene derivatives in a direct and regioselective manner. The process involves an anionic cyclization on a benzyne-tethered aryllithium intermediate.
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