102593-53-3Relevant academic research and scientific papers
Iridium-catalyzed annulative coupling of 2-arylbenzoyl chlorides with alkynes: Selective formation of phenanthrene derivatives
Nagata, Tomoya,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
, p. 8960 - 8967 (2014)
2-Arylbenzoyl chlorides undergo annulative coupling with internal alkynes in the presence of a catalyst system of [IrCl(cod)]2/P(t-Bu)3 to selectively afford the corresponding phenanthrene derivatives accompanied by elimination of carbon monoxide and hydrogen chloride. The reaction occurs without addition of any external base. Deuterium-labeling experiments using 2-(d5-phenyl)benzoyl chloride suggest that the rate-determining step does not involve the C2′-H bond cleavage. Formation of a [(t-Bu)3PH][(biphenyl-2,2′-diyl)Ir(CO)Cl2] complex dimer, of which the structure was determined by single-crystal X-ray analysis, from a stoichiometric reaction at 60 °C without addition of alkyne also supports the facile C-H cleavage.
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.
Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives
Nagata, Tomoya,Satoh, Tetsuya,Nishii, Yuji,Miura, Masahiro
, p. 1707 - 1710 (2016/07/06)
A rhodium-catalyzed annulative coupling of (2-arylphenyl)boronic acids with alkynes has been developed for the facile construction of phenanthrene frameworks. The reaction proceeded without external bases, and dioxygen worked as a terminal oxidant. Deuter
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
Synthesis of fluorenes via the palladium-catalyzed 5-exo-dig annulation of o-alkynylbiaryls
Chernyak, Natalia,Gevorgyan, Vladimir
scheme or table, p. 1101 - 1114 (2009/12/07)
The direct palladium-catalyzed intramolecular hydro arylation of o-alkynylbiaryls proceeded in a highly stereoselective manner producing fluorenes 2, the products of 5-exo-dig cyclization, in excellent yields. The cascade intermolecular arylation, incorpo
