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A Route to Regioselectively Functionalized Carbazoles, Dibenzofurans, and Dibenzothiophenes through Anionic Cyclization of Benzyne-Tethered Aryllithiums
journal contribution
posted on 2006-08-04, 00:00 authored by Roberto Sanz, Yolanda Fernández, M Castroviejo, Antonio Pérez, Francisco J. FañanásThe 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.