1198351-29-9Relevant articles and documents
Cercosporin-bioinspired photoreductive activation of aryl halides under mild conditions
Tang, Zhaocheng,Li, Jia,Lin, Fulin,Bao, Wenhao,Zhang, Shiwei,Guo, Baodang,Huang, Shuping,Zhang, Yan,Rao, Yijian
, p. 1 - 8 (2019)
Bioinspired by the naturally-occurring cercosporin-driven infection process of plant pathogenic fungi Cercospora sp., here we took advantage of the photophysical properties of cercosporin, and used it as a metal-free photocatalyst to develop an unpreceden
Halogen bonding matters: Visible light-induced photoredox catalyst-free aryl radical formation and its applications
Fang, Yu.,Liu, Fengyi,Ma, Jiani,Miao, Rong,Wang, Dan,Xiao, Jianliang,Xue, Dong
, p. 10212 - 10218 (2020/06/30)
Photo-involving aryl halide activation plays a pivotal role in organic synthesis and materials science. Revealing the mechanism and understanding the photophysical and photochemical processes in the activation is of great importance. Here, we found that a
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.
Biaryl Cross-Coupling Enabled by Photo-Induced Electron Transfer
Hayashi, Hirohito,Wang, Bin,Wu, Xiangyang,Teo, Shi Jie,Kaga, Atsushi,Watanabe, Kohei,Takita, Ryo,Yeow, Edwin K. L.,Chiba, Shunsuke
supporting information, p. 2223 - 2231 (2020/04/30)
We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls. (Figure presented.).
Visible light catalysis method for dehalogenation of aryl halide without need of photooxidation reduction catalyst
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Paragraph 0057; 0069; 0062, (2018/06/16)
The invention discloses a visible light catalysis method for dehalogenation of aryl halide without the need of a photooxidation reduction catalyst, and belongs to the technical field of visible lightcatalysis organic synthesis. The method comprises the following steps that firstly, the aryl halide is weighed and placed in a reaction vessel, and a solvent is added; secondly, the reaction vessel isfilled with nitrogen for oxygen removal for 0-50 minutes, and alkali is added during the oxygen removal period; thirdly, the reaction vessel is sealed and placed over a light emitting diode with thewavelength of 400-500 nm and the power of 0.5-30 W for irradiation, and reacting is conducted for 3-48 hours at room temperature under the condition of stirring and then finished. By means of the method, the photooxidation reduction catalyst which is high in price or complex in synthesis is not needed, reacting can be achieved under the condition of the room temperature or under a mild condition,a reaction substrate is high in adaptability, and the reaction yield is high.
Direct arylation of pyrrole derivatives in superbasic media
Vakuliuk, Olena,Koszarna, Beata,Gryko, Daniel T.
experimental part, p. 2833 - 2837 (2011/10/18)
Direct arylation of N-alkyl- and N-arylpyrroles with aryl iodides can be performed in superbasic media, without external addition of a transition-metal catalyst. Lithium hydroxide in dimethyl sulfoxide promotes this reaction in a regioselective manner, le
Base-mediated direct arylation of pyrrole derivatives
Vakuliuk, Olena,Koszarna, Beata,Gryko, Daniel T.
supporting information; experimental part, p. 925 - 930 (2011/06/20)
It appears that transition metal catalysts are not necessary to perform the direct arylation of electron-rich heterocycles with aryl iodides and bromides. Lithium tert-butoxide in DMF promotes this reaction for a variety of N-alkyl- and N-arylpyrroles as
Direct arylation of pyrrole derivatives in ionic liquids
Vakuliuk, Olena,Gryko, Daniel T.
experimental part, p. 2854 - 2859 (2011/06/26)
An efficient methodology for the direct arylation of pyrrole derivatives has been developed. The reaction proceeds smoothly with a wide range of structurally diverse aryliodides. Derivatives bearing an N,N-dimethylamino group at the 1-position and an aryl substituent at the 2-position were prepared for the first time. This protocol is more environmentally friendly than those previously reported because it is free of transition metals and utilizes ionic liquids rather than volatile organic solvents.
Palladium-catalyzed 2-arylation of pyrroles
Gryko, Daniel T.,Vakuliuk, Olena,Gryko, Dorota,Koszarna, Beata
supporting information; experimental part, p. 9517 - 9520 (2010/03/24)
(Chemical Equation Presented) A methodology that affords N-alkyl-2-arylpyrroles and N-aryl-2-arylpyrroles via direct coupling from aryl iodides has been developed. After examining various reaction parameters: solvent, ratio of reagents, catalyst, base and
