Journal Article Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Brønsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol

Fujita, Takeshi  ,  Takahashi, Ikko  ,  Hayashi, Masaki  ,  Wang, Jingchen  ,  Fuchibe, Kohei  ,  Ichikawa, Junji

2017 ( 2 )  , pp.262 - 265 , 2017-01 , WILEY-VCH
The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Brønsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the α-position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.

Number of accesses :  

Other information