125610-77-7Relevant academic research and scientific papers
Synthesis of Novel 4,4-Dialkyl- and 4,4-Diarylindeno[1,2-b]Thiophenes and their 2-Bromo Derivatives
Bucevicius, J.,Tumkevicius, S.,Adomenasp, P.
, p. 1413 - 1420 (2015)
A series of new 4,4-dialkyl- and 4,4-diaryl-4H-indeno[1,2-b]thiophenes and their 2-bromo derivatives were synthesized and characterized. An economical one-pot method for the preparation of the key starting material 2-(2-thienyl)benzoic acid and improved p
A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry
Constantin, Timothée,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.
, p. 12822 - 12828 (2020/12/29)
The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp2 C-P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process.
UiO-66 microcrystals catalyzed direct arylation of enol acetates and heteroarenes with aryl diazonium salts in water
Sun, Zhong-Hua,Chen, Wang,Qian, Bing-Bing,Wang, Liang,Yu, Binxun,Chen, Qun,He, Ming-Yang,Zhang, Zhi-Hui
, (2020/01/25)
UiO-66 is a classic Metal–organic framework (MOF) that constructed by zirconium cations and terephthalate with high chemical and thermal stability. Using pristine UiO-66 nanocrystals as the catalysts, the carbon–carbon bond formation based on denitrogenat
Anthraquinones as Photoredox Catalysts for the Reductive Activation of Aryl Halides
Bardagi, Javier I.,Ghosh, Indrajit,Schmalzbauer, Matthias,Ghosh, Tamal,K?nig, Burkhard
supporting information, p. 34 - 40 (2018/01/01)
Quinones are ubiquitous in nature as structural motifs in natural products and redox mediators in biological electron-transfer processes. Although their oxidation properties have already been used widely in chemical and photochemical reactions, the applications of quinones in reductive photoredox catalysis are less explored. We report the visible-light photoreduction of aryl halides (Ar–X; X = Cl, Br, I) by 1,8-dihydroxyanthraquinone. The resulting aryl radical anions fragment into halide anions and aryl radicals, which react through hydrogen abstraction or C–C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion. Subsequent visible-light excitation of the anthraquinone radical anion or semiquinone anion converts them into very potent single-electron donors. A plausible mechanism for the reaction is proposed on the basis of control experiments and spectroscopic investigations.
Unexpected dual role of titanium dioxide in the visible light heterogeneous catalyzed C-H arylation of heteroarenes
Zoller, Jochen,Fabry, David C.,Rueping, Magnus
, p. 3900 - 3904 (2015/06/16)
The direct arylation of heteroaromatics with an easily accessible and recyclable, heterogeneous TiO2 catalyst and visible light was developed. Electron-rich as well as electron-poor heteroarenes could be applied in this transformation, and the corresponding products were isolated in very good yields. Azoethers were detected as reactive intermediates, and the unexpected role of TiO2 in their formation as well as reaction was established.
Synthesis of heteroaryl compounds through cross-coupling reaction of aryl bromides or benzyl halides with thienyl and pyridyl aluminum reagents
Chen, Xu,Zhou, Lingmin,Li, Yimei,Xie, Tao,Zhou, Shuangliu
, p. 230 - 239 (2014/01/17)
An efficient method for synthesis of useful biaryl building blocks containing 2-thienyl, 3-thienyl, 2-pyridyl, and 3-pyridyl moieties was provided through cross-coupling reactions of aryl bromides or benzyl halides with heteroaryl aluminum reagents in the presence of Pd(OAc)2 and (o-tolyl)3P. The coupling reaction also worked efficiently with heteroaryl bromides affording series of heterobiaryl compounds. The reaction of phenylbromide with in situ prepared 3-pyridyl aluminum was demonstrated to afford the product 8a in high yield. Additionally, the catalytic system was also suited well for the coupling reaction of benzyl halides with pyridyl aluminum reagents to afford series of pyridyl-arylmethane.
Palladium-catalyzed desulfitative cross-coupling of sodium arylsulfinates with aryl bromides and chlorides: An alternative convenient synthesis of biaryls
Zhou, Chao,Li, Yaming,Lu, Yang,Zhang, Rong,Jin, Kun,Fu, Xinmei,Duan, Chunying
, p. 1269 - 1273 (2013/11/06)
An alternative method for synthesis of biaryls has been developed through the Pd catalyzed desulfitative coupling reaction of sodium arylsulfinates with aryl bromides and chlorides. The procedure tolerates a variety of functional groups, such as cyano, formyl, acetyl, chloro, methoxy, trifluoromethyl and heteroaromatic unit. The desired products were obtained in moderate to excellent yields under relatively mild reaction conditions without additives, base or co-catalyst. An alternative method for synthesis of biaryls has been developed through the Pd catalyzed desulfitative coupling reaction of sodium arylsulfinates with aryl bromides and chlorides. The procedure tolerates a variety of functional groups, such as cyano, formyl, acetyl, chloro, methoxy, trifluoromethyl and heteroaromatic unit. The desired products were obtained in moderate to excellent yields under relatively mild reaction conditions without additives, base or co-catalyst. Copyright
Palladium-catalyzed intermolecular desulfinylative cross-coupling of heteroaromatic sulfinates
Sévigny, Stéphane,Forgione, Pat
supporting information, p. 2256 - 2260 (2013/03/28)
Beauty lies in simplicity: An efficient and environmentally benign palladium-catalyzed protocol has been developed using a sulfinate as a nucleophilic coupling partner. The sulfinate position is arylated chemoselectively in very good yields. The bench-stable, non-hygroscopic heteroaromatic sulfinate salts rapidly undergo cross-coupling without the need of a co-catalyst, base, or additives (see scheme; mw=microwave). Copyright
Efficient desulfinylative cross-coupling of thiophene and furan sulfinates with aryl bromides in aqueous media
Sévigny, Stéphane,Forgione, Pat
supporting information, p. 589 - 592 (2013/04/10)
This letter describes the development of an environmentally benign palladium-catalyzed cross-coupling reaction using heteroaromatic sulfinates as nucleophilic coupling partners in aqueous media. This method accesses aryl-substituted heteroaromatics in very good yields chemoselectively without the need for base, additives or co-catalysts.
