725213-67-2Relevant articles and documents
Extended Study of Visible-Light-Induced Photocatalytic [4 + 2] Benzannulation: Synthesis of Polycyclic (Hetero)Aromatics
Chatterjee, Tanmay,Lee, Da Seul,Cho, Eun Jin
, p. 4369 - 4378 (2017/04/28)
Herein we report an extended study of [4 + 2] benzannulation reactions of 2-(hetero)aryl-substituted anilines with alkynes by visible light photocatalysis. The method requires the use of tBuONO as a diazotizing agent and 0.3 mol % of fac-Ir(ppy)3 as a photocatalyst at room temperature. The reaction proceeded in a chemo- and regioselective manner with high functional group tolerance under mild conditions allowing the preparation of a wide variety of polycyclic (hetero)aromatic compounds, including phenanthrenes, in moderate to high yields. This procedure is amenable to gram-scale synthesis of 9-phenylphenanthrene.
Phenanthrene synthesis by eosin Y-catalyzed, visible light- Induced [4+2] benzannulation of biaryldiazonium salts with alkynes
Xiao, Tiebo,Dong, Xichang,Tang, Yanchi,Zhou, Lei
supporting information, p. 3195 - 3199 (2013/01/16)
A metal-free, visible light-induced [4+2] benzannulation of biaryldiazonium salts with alkynes was developed. With eosin Y as photoredox catalyst, a variety of 9-substituted or 9,10-disubstituted phenanthrenes were obtained via a cascade radical addition and cyclization sequence. Copyright
Chromium-mediated synthesis of polycyclic aromatic compounds from halobiaryls
Kanno, Ken-Ichiro,Liu, Yuanhong,Iesato, Atsushi,Nakajima, Kiyohiko,Takahashi, Tamotsu
, p. 5453 - 5456 (2007/10/03)
(Chemical Equation Presented) Reaction of 2,2′-dihalobiphenyl with butyllithium followed by the addition of chromium(III) chloride and alkynes afforded the corresponding phenanthrene derivatives via formal [4 + 2] cycloaddition. A variety of alkynes could be used for this reaction, such as alkyl, aryl, silyl, and alkoxycarbonyl alkynes. Repetitive process of the reaction gave more extended polycyclic compounds such as benzo[g]chrysene and azacyclopentaphenalene derivatives.