Li, Chia-Wen Wang, Cheng-I Liao, Hsin-Yi Chaudhuri, Rupsha Liu, Rai-Shung Synthesis of Dibenzo[<i>g,p</i>]chrysenes from Bis(biaryl)acetylenes via Sequential ICl-Induced Cyclization and Mizoroki−Heck Coupling We report a facile synthesis of functionalized dibenzo[<i>g</i>,<i>p</i>]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[<i>g</i>,<i>p</i>]chrysenes bearing various functionalities. With substrates of one special type including 4‘-methoxy-2-ethynylbiphenyls, we found that the ICl treatment led to <i>ipso</i> cyclization to give bicyclic spirocyclohexadienones. In the presence of MeOH/H<sub>2</sub>SO<sub>4</sub>, 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 <i>ipso</i> cyclization and 1,2-alkenyl shift. This <i>ipso</i>-cyclization approach can be extended to the preparation of dibenzo[<i>g</i>,<i>p</i>]chrysenes. Mizoroki;ICl treatment;cyclization approach;spiroketone products;methoxy;chrysene;alkenyl;approach works;functionalized dibenzo;bicyclic spirocyclohexadienones 2007-11-23
    https://acs.figshare.com/articles/dataset/Synthesis_of_Dibenzo_i_g_p_i_chrysenes_from_Bis_biaryl_acetylenes_via_Sequential_ICl_Induced_Cyclization_and_Mizoroki_Heck_Coupling/2972836
10.1021/jo701504m.s006