135489-54-2Relevant academic research and scientific papers
A route to regioselectively functionalized carbazoles, dibenzofurans, and dibenzothiophenes through anionic cyclization of benzyne-tethered aryllithiums
Sanz, Roberto,Fernandez, Yolanda,Castroviejo, Ma. Pilar,Perez, Antonio,Fananas, Francisco J.
, p. 6291 - 6294 (2007/10/03)
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.
A CONVENIENT PREPARATION OF STERICALLY CROWDED 1,9-DISUBSTITUTED DIBENZOTHIOPHENES AND 3,3'-DISUBSTITUTED DIARYL SULFIDES
Furukawa, Naomichi,Kimura, Takeshi,Horie, Yoji,Ogawa, Satoshi
, p. 675 - 678 (2007/10/02)
Thianthrene-5-oxide (1) reacted with 2.2 equivalents of lithium diisopropylamide to give 4,6-dilithiated 1 which was converted to 4,6-disubstituted thianthrene-5-oxides (3). 3 afforded sterically crowded 1,9-disubstituted dibenzothiophenes (4) in moderate yields on treatment with n-butyllithium or phenyllithium.
