5235-80-3Relevant academic research and scientific papers
The One-electron Oxidation of Biphenyl-2-ylethylenes. Subsequent Chemical Reactivity Controlled by Electron Return or Proton Transfer
Lapouyade, Rene,Villeneuve, Patrice,Nourmamode, Aziz,Morand, Jean-Pierre
, p. 776 - 778 (1987)
Biphenyl-2-ylethylenes react with (4-BrC6H4)3N.+SbCl6- to give the radical cation of the electrocyclization product which initiates a protic catalysis to the related flourenes or, in presence of 2,6-di-t-butylpyridine or water, lead
Au-Catalyzed Biaryl Coupling to Generate 5- To 9-Membered Rings: Turnover-Limiting Reductive Elimination versus ?-Complexation
Ball, Liam T.,Corrie, Tom J. A.,Lloyd-Jones, Guy C.,Russell, Christopher A.
, p. 245 - 254 (2021/09/04)
The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes - substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to ?-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the ?-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.
Efficient synthesis of 9-aryldihydrophenanthrenes by a cascade reaction involving arynes and styrenes
Bhojgude, Sachin Suresh,Bhunia, Anup,Gonnade, Rajesh G.,Biju, Akkattu T.
supporting information, p. 676 - 679 (2014/03/21)
A mild, general, and transition-metal-free protocol for the synthesis of 9,10-dihydrophenanthrenes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes an efficient cascade reaction initiated by the Diels-Alder reaction with the differently substituted styrenes leading to the formation of 9-aryl-9,10-dihydrophenanthrene derivatives in moderate to good yields.
Triflic acid promoted synthesis of polycyclic aromatic compounds
Li, Ang,DeSchepper, Daniel J.,Klumpp, Douglas A.
scheme or table, p. 1924 - 1927 (2009/09/05)
The triflic acid (CF3SO3H) promoted cyclizations of 2-styrylbiaryls are found to be useful for the synthesis of polycyclic aromatic compounds, including functionalized derivatives of polycyclic aromatic compounds and heterocyclic sys
Functionalized (Benzotriazol-1-yl)methanes as 1,1-Dipole Synthon Equivalents in Diverse Annulations to Aromatic and Heteroaromatic Rings
Katritzky, Alan R.,Wang, Xiaojing,Xie, Linghong,Toader, Dorin
, p. 3445 - 3449 (2007/10/03)
The title compounds 1a-e readily undergo deprotonation and subsequent reactions with the appropriate electrophiles to form intermediates of types 4 and 7 which, upon treatment with Lewis acids, cyclize to afford fused aromatics 5 and 8. Tetrahydronaphthalene 11a, 1,2,3,4-tetrahydrochromanes (11b-d, 13), indanes (16, 18), 9,10-dihydrophenanthrenes (21a-c, 25), and tetrahydro[1,2-α]indoles (28, 30) with phenyl, substituted phenyl, and thienyl substituents were prepared in this manner.
