24691-94-9Relevant academic research and scientific papers
A metal-free picolinamide assisted electrochemical ortho-trifluoromethylation of arylamines
Wang, Kai,Hou, Jiahao,Wei, Tingting,Zhang, Changjun,Bai, Renren,Xie, Yuanyuan
supporting information, (2020/12/21)
An eco-friendly and effective electrochemical process was developed for the ortho-trifluoromethylation of arylamines using CF3SO2Na as the trifluoromethyl source, affording the desired products in moderate to good yields with high regioselectivity under mild reaction conditions. Importantly, the requirement for both transition metals and oxidants utilized in previous methods were avoided. A radical mechanism was proposed on the basis of various control experiments.
Visible-Light-Mediated Nickel(II)-Catalyzed C-N Cross-Coupling in Water: Green and Regioselective Access for the Synthesis of Pyrazole-Containing Compounds
You, Guirong,Wang, Kai,Wang, Xiaodan,Wang, Guodong,Sun, Jian,Duan, Guiyun,Xia, Chengcai
supporting information, p. 4005 - 4009 (2018/07/22)
A regioselective green approach for the nickel(II)-catalyzed C-N cross-coupling between arylamines and pyrazoles through a photoredox process is reported. Moderate to good yield was observed for this reaction, performed in water under air at room temperature. This strategy provides a powerful tool for the green synthesis of pyrazole-containing bioactive molecules. In addition, a single-electron-transfer mechanism is proposed in this report.
Iron-catalyzed: Ortho trifluoromethylation of anilines via picolinamide assisted photoinduced C-H functionalization
Xia, Chengcai,Wang, Kai,Wang, Guodong,Duan, Guiyun
supporting information, p. 2214 - 2218 (2018/04/05)
A convenient, oxidant-free protocol was developed for the ortho trifluoromethylation of aniline via picolinamide assisted Fe-promoted C-H functionalization under ultraviolet irradiation. In this transformation acetone essentially acted as both a solvent to dissolve reactants and a low-cost radical initiator to efficiently generate a CF3 radical from Langlois' reagent. A broad substrate scope was tolerated and picolinamide bearing strong electron withdrawing groups also could be transformed into the corresponding products with acceptable yields. Furthermore, the value of this method has been highlighted via the efficient synthesis of the nonsteroidal anti-inflammatory drug floctafenine.
Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines
Yang, Qi-Liang,Wang, Xiang-Yang,Lu, Jia-Yan,Zhang, Li-Pu,Fang, Ping,Mei, Tian-Sheng
supporting information, p. 11487 - 11494 (2018/09/13)
Electrochemical oxidation represents an environmentally friendly solution to conventional methods that require caustic stoichiometric chemical oxidants. However, C-H functionalizations merging transition-metal catalysis and electrochemical techniques are, to date, largely confined to the use of precious metals and divided cells. Herein, we report the first examples of copper-catalyzed electrochemical C-H aminations of arenes at room temperature using undivided electrochemical cells, thereby providing a practical solution for the construction of arylamines. The use of n-Bu4NI as a redox mediator is crucial for this transformation. On the basis of mechanistic studies including kinetic profiles, isotope effects, cyclic voltammetric analyses, and radical inhibition experiments, the reaction appears to proceed via a single-electron-transfer (SET) process, and a high valent Cu(III) species is likely involved. These findings provide a new avenue for transition-metal-catalyzed electrochemical C-H functionalization reactions using redox mediators.
Copper-catalyzed carboxamide-directed ortho amination of anilines with alkylamines at room temperature
Li, Qiong,Zhang, Shu-Yu,He, Gang,Ai, Zhaoyan,Nack, William A.,Chen, Gong
supporting information, p. 1764 - 1767 (2014/04/17)
In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.
APPLICATIONS of ORGANOLITHIUM and RELATED REAGENTS in SYNTHESIS. Part V. Directed Metallation of Secondary Picolin- and Isonicotinamides. A Useful Method for the Synthesis of 2,3- and 3,4-Disubstituted Pyridines, Including Furopyridin-3(1H)-one and Furopyridine-1(3H)-one
Epsztajn, Jan,Bieniek, Adam,Plotka, Mieczyslaw W.
, p. 442 - 474 (2007/10/02)
The metallation reaction of N-methyl-, N-benzyl- and N-phenyl-amides (1a-c) and (2a-c) derived from picolinic and isonicotinic acids by BunLi in THF leading to the corresponding bis(N- and 3-)lithiated amides (3a-c) and (4a-c), are described.The N-phenylamides (anilides) (1c) and (2c), in comparison with the other aliphatic derivatives, demonstrate greater abilities to direct ortho lithiation at the 3-position of the pyridine ring, and give with very good yields bis(N- and 3-)lithiated anilides (3c) and (4c), respectively.The N-benzylamides (1b) and (2b) are ortho metallated under kinetic control at -78 deg C to form the bis(N- and 3-)lithiated benzylamides (3b) and (4b), but the organometallic intermediates rearrange at room temperature to give the thermodynamically more stable bis(N- and α-)lithiated amides (3g) and (4g) (benzyl-type anions).The generated carbanions (3c), (4c), (3g) and (4g) were trapped by a variety of electrophiles (e.g. alkyl halides and aldehydes).The synthesis of furopyridin-3(1H)-one (18) and furopyridin-(3H)-one (19) is included.
THE DUAL BEHAVIOUR OF N,N-DIALKYLPYRIDYLCARBOXYLIC AMIDES IN THE REACTION WITH LITHIUM DIISOPROPYLAMIDE
Epsztajn, Jan,Bieniek, Adam,Brzezinski, Jacek Z.,Jozwiak, Andrzej
, p. 4735 - 4738 (2007/10/02)
The dual behaviour of N,N-diisopropylpyridylcarboxylic amides in the reaction with iPr2NLi depending upon temperature and structure of a given amide, is described.
Fungicidal dispersions of carboxylic acid amides
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, (2008/06/13)
Fungicidal dispersions comprising a carboxylic acid amide, other than pyracarbolide, as the fungicidally-active ingredient and an aluminum chelate of a polynuclear hydroxy-quinone as a crystal growth stabilizer, dispersed in a paraffinic mineral oil, a liquid triglyceride, or a liquid ester formed between a C1 -C12 monoalcohol and a C2 -C10 mono- or di-carboxylic acid.
