52168-00-0Relevant articles and documents
Bis(pentafluorophenyl)-: O-carborane and its arylthio derivatives: Synthesis, electrochemistry and optical properties
Eguchi, Hiroshi,Inagi, Shinsuke,Nishikawa, Takanobu,Owaki, Satoshi,Shida, Naoki,Tomita, Ikuyoshi
supporting information, p. 12985 - 12989 (2020/10/13)
Synthesis of 1,2-bis(pentafluorophenyl)-o-carborane and its arylthio-derivatives is reported. The regioselective arylthiolation was successfully achieved via nucleophilic aromatic substitution (SNAr) reaction. A series of bis(perfluoroaryl)-o-carboranes w
Halo-1,2,3-triazolium salts as halogen bond donors for the activation of imines in dihydropyridinone synthesis
Kaasik, Mikk,Metsala, Andrus,Kaabel, Sandra,Kriis, Kadri,J?rving, Ivar,Kanger, Tonis
, p. 4295 - 4303 (2019/03/29)
In the past decade halogen bond (XB) catalysis has gained considerable attention. Halo-triazoles are known XB donors, yet few examples detail their use as catalysts. As a continuation of our previous work the catalytic properties of substituted enantiomerically pure halo-triazolium salts were explored in the reaction between an imine and Danishefsky's diene leading to the formation of dihydropyridinone. The catalytic activity of the XB donors was highly dependent on the choice of the halogen atom and on the counterion. Also, it was found that impurities in the diene affected the rate of the reaction.
Systematic Experimental and Computational Studies of Substitution and Hybridization Effects in Solid-State Halogen Bonded Assemblies
Nguyen, Suong T.,Ellington, Thomas L.,Allen, Katelyn E.,Gorden, John D.,Rheingold, Arnold L.,Tschumper, Gregory S.,Hammer, Nathan I.,Watkins, Davita L.
, p. 3244 - 3254 (2018/05/09)
A quantitative assessment of the substituent, hybridization, and crystal-packing effects on the electronic, structural, and vibrational properties of halogen bonded systems is presented. Through a combined experimental and theoretical approach employing R
Arylation, Vinylation, and Alkynylation of Electron-Deficient (Hetero)arenes Using Iodonium Salts
Liu, Chuan,Wang, Qiu
supporting information, p. 5118 - 5121 (2016/10/14)
Arylation, vinylation, and alkynylation of electron-deficient arenes and heteroarenes have been achieved by chemoselective C-H zincation followed by copper-catalyzed coupling reactions using iodonium salts. This approach offers a direct and general access to a wide scope of (hetero)biaryls as well as alkenylated and alkynylated heteroarenes under mild conditions. It is particularly useful and valuable for the rapid and modular synthesis of diverse (hetero)aryl compounds, as demonstrated in the synthesis of transient receptor potential vanilloid 1 (TRPV1) antagonists and angiotensin II receptor type 1 (AT1 receptor) antagonists.
Halogen bonding of (iodoethynyl)benzene derivatives in solution
Dumele, Oliver,Wu, Dino,Trapp, Nils,Goroff, Nancy,Diederich, Francois
supporting information, p. 4722 - 4725 (2015/04/27)
Halogen bonding (XB) between (iodoethynyl)benzene donors and quinuclidine in benzene affords binding free enthalpies (δG, 298 K) between -1.1 and -2.4 kcal mol-1, with a strong LFER with the Hammett parameter σpara. The enthalpic dri
Metal-free 1,5-regioselective azide-alkyne [3+2]-cycloaddition
Kloss, Florian,Koehn, Uwe,Jahn, Burkhard O.,Hager, Martin D.,Goerls, Helmar,Schubert, Ulrich S.
supporting information; experimental part, p. 2816 - 2824 (2012/06/01)
[3+2]-cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5-disubstituted-4-(trimethyl-silyl)-1H-1,2,3-triazoles. The formation of the 1,5-isomer is highly favored in this metal-free cycloaddition, which could be proven by 1D selective NOESY and X-ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5-isomer. The described method provides a simple alternative protocol to metal-catalyzed "click chemistry" procedures, widening the scope for regioselective heavy-metal-free synthetic applications.
Fluoro-substituted phenyleneethynylenes: Acetylenic n-type organic semiconductors
Matsuo, Daisuke,Yang, Xin,Hamada, Akiko,Morimoto, Kyo,Kato, Takuji,Yahiro, Masayuki,Adachi, Chihaya,Orita, Akihiro,Otera, Junzo
supporting information; experimental part, p. 1300 - 1302 (2011/02/17)
Fluoro-substituted phenyleneethynylenes are synthesized by Sonogashira coupling and acetylide-nucleophilic substitution of fluorobenzenes. Fluoro-substitution of benzenes enables deep LUMO potential, and CF 3-substitution provides high electron
Palladium-catalysed Alkynyl-dehydroxylation of Polyfluorophenols
Chen, Qing-Yun,Li, Zhan-Ting
, p. 2931 - 2934 (2007/10/02)
Treatment of polyfluorophenyl perfluoroalkanesulfonates RfSO3C6H4X-p (1, X = F, Cl) with alkynes in the presence of Pd(PPh3)2Cl2 or Pd(PP3)4 and Et3N in DMF gave polyfluorophenylalkynes in good to high yields.The same products were also prepare
A Convenient Synthesis of Bis(polyfluorophenyl)butadiyne Monomers
Zhang, Yadong,Wen, Jianxun
, p. 727 - 728 (2007/10/02)
1,4-Bis(polyfluorophenyl)butadiynes were prepared in high yields by nucleophilic substitutions on the 1,4-bis(pentafluorophenyl)butadiyne which was prepared in three steps from pentafluoroiodobenzene and trimethylsilylacetylene.
