99-12-7Relevant articles and documents
Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
, p. 9561 - 9568 (2021/08/06)
A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.
N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids
Budinská, Alena,Katayev, Dmitry,Passera, Alessandro,Zhang, Kun
supporting information, (2020/03/30)
Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.
Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.
supporting information, (2019/09/07)
A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.
Ipso-nitration of arylboronic acids with copper nitrate and trifluoroace-tic acid
Wang, Zhu-Qing,Guo, Meng-Ping,Wen, Yong-Ju,Shen, Xiu-Li,Lv, Mei-Yun,Zhou, Xiu-Ling
, p. 891 - 894 (2018/11/06)
An efficient and novel nitrating reagent has been developed for ipso-nitration of arylboronic acids. By using inexpensive and commercially available Cu(NO3)2/CF3COOH as nitrating reagent, various nitroarenes are produced in moderate to excellent yields (51-96%). Advantages of this procedure are the operational simplicity and no need of extra catalyst.
Synthetic method for 1,5-bis(chloromethyl)-3-fluorobenzene
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Paragraph 0007, (2017/02/17)
The invention discloses a synthetic method for 1,5-bis(chloromethyl)-3-fluorobenzene, which belongs to the field of chemical synthesis. The synthetic method comprises the following steps: adding concentrated sulfuric acid and fuming nitric acid into 3,5-dimethylchlorobenzene and carrying out a reaction in an ice bath so as to obtain 3,5-dimethylnitrobenzene; then adding ethanol and palladium charcoal and introducing hydrogen so as to obtain 3,5-dimethylaniline; allowing 3,5-dimethylaniline and tetrafluoroboric acid to undergo an ice bath and adding a sodium nitrite solution drop by drop; carrying out filtering after completion of addition and drying obtained filter residue; and placing the filter residue in a flask for decomposition, adding water and petroleum ether and carrying out distillation so as to obtain 1,5-bis(chloromethyl)-3-fluorobenzene.
Caged CO2 for the Direct Observation of CO2-Consuming Reactions
Lommel, Katharina,Sch?fer, Gabriela,Grenader, Konstantin,Ruland, Christoph,Terfort, Andreas,M?ntele, Werner,Wille, Georg
, p. 372 - 380 (2013/08/24)
CO2-consuming reactions, in particular carboxylations, play important roles in technical processes and in nature. Their kinetic behavior and the reaction mechanisms of carboxylating enzymes are difficult to study because CO2 is inconvenient to handle as a gas, exists in equilibrium with bicarbonate in aqueous solution, and typically yields products that show no significant spectroscopic differences from the reactants in the UV/Vis range. Here we demonstrate the utility of 3-nitrophenylacetic acid and related compounds (caged CO2) in conjunction with infrared spectroscopy as widely applicable tools for the investigation of such reactions, permitting convenient measurement of the kinetics of CO2 consumption. The use of isotopically labeled caged CO2 provides a tool for the assignment of infrared absorption bands, thus aiding insight into reaction intermediates and mechanisms.
Copper-catalyzed nitration of arylboronic acids with nitrite salts under mild conditions: An efficient synthesis of nitroaromatics
Yan, Guobing,Zhang, Ling,Yu, Jian
experimental part, p. 133 - 137 (2012/07/28)
Copper-catalyzed nitration of arylboronic acids has been developed with nitrite salts as nitrating agent under mild conditions. This process provides an efficient and practical method for the synthesis of nitro aromatics, due to its simple experimental procedure and its use of convenient and inexpensive copper catalyst.
Green and controllable metal-free nitrification and nitration of arylboronic acids
Wang, Shuai,Shu, Chun Chun,Wang, Tao,Yu, Jian,Yan, Guo Bing
scheme or table, p. 643 - 646 (2012/08/07)
A novel and green nitrating reagent has been developed for the nitrification and nitration of arylboronic acids, which can be controlled by the reaction conditions. The process provides an attractive alternative to the traditional nitration protocols.
Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics
Fors, Brett P.,Buchwald, Stephen L.
scheme or table, p. 12898 - 12899 (2009/12/07)
(Chemical Equation Presented) An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent
