Details

Autor(en) / Beteiligte

• Li, Chia-Wen
• Wang, Cheng-I
• Liao, Hsin-Yi
• Chaudhuri, Rupsha
• Liu, Rai-Shung

Titel

Synthesis of Dibenzo[g,p]chrysenes from Bis(biaryl)acetylenes via Sequential ICl-Induced Cyclization and Mizoroki−Heck Coupling

Ist Teil von

• Journal of organic chemistry, 2007-11, Vol.72 (24), p.9203-9207

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2007

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• We report a facile synthesis of functionalized dibenzo[g,p]chrysenes via initial ICl-promoted cyclization of bis(biaryl)acetylenes, followed by the Mizoroki−Heck coupling reaction. This new approach works well for various bis(biaryl)acetylenes to afford dibenzo[g,p]chrysenes bearing various functionalities. With substrates of one special type including 4‘-methoxy-2-ethynylbiphenyls, we found that the ICl treatment led to ipso cyclization to give bicyclic spirocyclohexadienones. In the presence of MeOH/H2SO4, these spiroketone products undergo rearrangement to give 9-iodophenanthrenes through a selective 1,2-alkenyl migration. We prepared various 4‘-methoxy-2-ethynylbiphenyl compounds to show the generalization of such an ipso cyclization and 1,2-alkenyl shift. This ipso-cyclization approach can be extended to the preparation of dibenzo[g,p]chrysenes.