Hoffmann Hendrik, Mukanov Diana, Ganschow Michael, Rominger Frank, Freudenberg Jan, Bunz Uwe H F
Organisch-Chemisches Institut , Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270 , 69120 Heidelberg , Germany.
InnovationLab , Speyerer Str. 4 , 69115 Heidelberg , Germany.
J Org Chem. 2019 Aug 2;84(15):9826-9834. doi: 10.1021/acs.joc.9b01567. Epub 2019 Jul 24.
We efficiently synthesized otherwise difficult to obtain 2,3- and 2,3,6,7-halogenated anthracenes with diverse east/west substituents. Key steps involve the (i) Vollhardt cyclization of bis(propargyl)benzenes with bis(trimethylsilyl)acetylene, (ii) halo-desilylation introducing chlorine, bromine, or iodine substituents, and (iii) dehydrogenation. Pd catalysis allows selective functionalization at the anthracenes' east/west positions. A tetrahydropentacene is synthesized and derivatized via the same strategy, employing tetrapropargylbenzene.
我们高效合成了带有不同东/西取代基、否则难以获得的2,3-和2,3,6,7-卤代蒽。关键步骤包括：(i) 双（炔丙基）苯与双（三甲基甲硅烷基）乙炔的福尔哈特环化反应；(ii) 引入氯、溴或碘取代基的卤代去硅基化反应；以及(iii) 脱氢反应。钯催化使得能够在蒽的东/西位置进行选择性官能化。通过相同策略，使用四炔丙基苯合成并衍生了一种四氢并五苯。
