17694-87-0Relevant academic research and scientific papers
Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives
Fard, Sara Tavakkoli,Sekine, Kohei,Farshadfar, Kaveh,Rominger, Frank,Rudolph, Matthias,Ariafard, Alireza,Hashmi, A. Stephen K.
supporting information, p. 3552 - 3559 (2021/02/05)
A simple gold-catalyzed annulation of 1,8-dialkynylnaphthalenes utilizing a cationic gold catalyst was developed. Such a peri-position of two alkynyl substituents has not been studied in gold catalysis before. Dependent on the substrate, the reactions either follow a mechanism involving vinyl cation intermediates or involve a dual gold catalysis mechanism which in an initial 6-endo-dig-cyclization generates gold(I) vinylidene intermediates that are able to insert into C?H bonds. Indenophenalene derivatives were obtained in moderate to high yields. In addition, the bidirectional gold-catalyzed annulation of tetraynes provided even larger conjugated π-systems. The optoelectronic properties of the products were also investigated.
Alumina-Mediated π-Activation of Alkynes
Akhmetov, Vladimir,Amsharov, Konstantin,Feofanov, Mikhail,Sharapa, Dmitry I.
supporting information, p. 15420 - 15426 (2021/09/30)
The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.
Synthesis and photoelectric properties of novel indeno[2,1-a]phenalene- based derivatives
Li, Duanqin,Liu, Miaochang,Chen, Jiuxi,Lan, Jian,Huang, Xiaobo,Wu, Huayue
, p. 389 - 396 (2013/04/24)
A series of novel indeno[2,1-a]phenalene derivatives 4a-j including electron-donating or electron-withdrawing groups were prepared by Pd-catalyzed Sonogashira-Hagihara reaction of 7-iodo-12-phenylindeno[2,1-a]phenalene with various arylacetylene. Photoele
Four iodine-mediated electrophilic cyclizations of rigid parallel triple bonds mapped from 1,8-dialkynylnaphthalenes
Chen, Xiaopeng,Lu, Ping,Wang, Yanguang
supporting information; experimental part, p. 8105 - 8114 (2011/09/13)
Four different types of fused arenes, including fluoranthene, indeno[2,1-a]phenalene, (8H)cyclopenta[a]acenaphthylene, and pyridine[a]acenaphthylene, were efficiently constructed through iodine-mediated electrophilic cyclizations of 1,8-dialkynyl naphthal
Palladium-catalyzed synthesis of 7,9-diaryl-8 H-acenaphtho[1,2-c]pyrroles and their application in explosives detection
Chen, Xiaopeng,Jin, Jisong,Wang, Yanguang,Lu, Ping
supporting information; experimental part, p. 9920 - 9923 (2011/10/09)
Making sensors of pyrroles: 7,9-Diarenyl-8H-acenaphtho[1,2-c]pyrroles were efficiently constructed by a palladium-catalyzed bicyclization of 1,8-diarenynyl naphthalenes and primary amines under air conditions (see scheme). The synthesized 8H-acenaphtho[1,
Intramolecular domino electrophilic and thermal cyclization of peri-ethynylene naphthalene oligomers
Huang, Xiaobo,Zeng, Lintao,Zeng, Zebing,Wu, Jishan
experimental part, p. 14907 - 14915 (2012/02/03)
The intramolecular electrophilic or thermal cyclization of arylene ethynylene precursors recently became a powerful method for the synthesis of new polycyclic aromatic hydrocarbons (PAHs). In this work, we investigated in detail the synthesis and intramol
Synthesis of fluoranthenes and indenocorannulenes: Elucidation of chiral stereoisomers on the basis of static molecular bowls
Wu, Yao-Ting,Hayama, Tomoharu,Baldridge, Kim K.,Linden, Anthony,Siegel, Jay S.
, p. 6870 - 6884 (2007/10/03)
Cycloaromatization of a peri diyne with an external alkyne provides a general route to indenofused polynuclear aromatics. Fluoranthenes 9 (or 13) are easily accessible in good to excellent yields (75-99%; 18 examples) from the reaction of symmetric (or as
Reaction of 1,8-Bis(phenylethynyl)naphthalene with Phenylchlorocarbene: Formation of an Intermolecular Cyclization Product from Carbene Monoadduct and of 1,8-Naphthylenebis(diphenylcyclopropenylium) Dication from the Bisadduct
Komatsu, Koichi,Arai, Mikiro,Hattori, Yoshiyuki,Fukuyama, Keiichi,Katsube, Yukiteru,Okamoto, Kunio
, p. 2183 - 2192 (2007/10/02)
The reactions of 1,8-bis(phenylethynyl)naphthalene (4) with phenylchloro- and dichlorocarbenes and chemistry of the obtained products have been studied.The reaction of 4 with 1 equiv of phenylchlorocarbene exclusively affords spirocyclopropene 8, whose st
