14547-72-9Relevant academic research and scientific papers
Copper-mediated ortho C–H primary amination of anilines
Cheng, Tai-Jin,Wang, Xing,Xu, Hui,Dai, Hui-Xiong
supporting information, (2021/05/10)
We report herein a copper-mediated ortho C–H primary amination of anilines by using cheap and commercially available benzophenone imine as the amination reagent. The protocol show good functional group tolerance and heterocyclic compatibility. Late-stage diversification of drugs demonstrate the synthetic utility of this protocol.
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.
Copper(ii) mediatedorthoC-H alkoxylation of aromatic amines using organic peroxides: efficient synthesis of hindered ethers
Ghosh, Subhash Chandra,Sahoo, Tapan,Sarkar, Souvik,Sen, Chiranjit
supporting information, p. 8949 - 8952 (2021/09/10)
Synthesis of hindered alkyl aryl ether derivatives (R-O-Ar) remains a huge challenge and highly desirable in organic and medicinal chemistry because extensive substitution on the ether bond prevents the undesired metabolic process and thus avoids rapid de
Method for selectively synthesizing halogenated arylamine through copper catalysis (by machine translation)
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Paragraph 0075-0078, (2020/12/30)
The method comprises the following steps: reacting a substrate with a halogenating reagent (III) in an organic solvent to obtain a catalyst. The reaction 0 - 80 °C is reacted at 0.5 - 6h under the action of an oxidizing agent, and after the reaction is finished, the reaction liquid is subjected to post-treatment to obtain the product halogenated aromatic amine compound. To the invention, direct synthesis of the halogenated aromatic amine compounds is achieved for the first time, and the problems that in the traditional method, the metal catalyst is expensive, the halogenated reagent toxicity is large, byproducts are large and the like are solved. At the same time, the product can take off the pyridine guide group through simple hydrolysis, and further functional groups can be combined into an aromatic heterocyclic compound. The method is simple and convenient to operate, mild in reaction conditions, high in selectivity, high in product yield and wide in substrate applicability, and is an efficient organic synthesis means. : Substrate: Halogenating agent: Product: (by machine translation)
Solvent-free iron(III) chloride-catalyzed direct amidation of esters
Mkhonazi, Blessing D.,Shandu, Malibongwe,Tshinavhe, Ronewa,Simelane, Sandile B.,Moshapo, Paseka T.
supporting information, (2020/03/17)
Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.
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.
Chelation-promoted Efficient C?H/N?H Cross Dehydrogenative Coupling between Picolinamides and Simple Ethers under Copper Catalysis
Yue, Qiang,Xiao, Zhen,Kuang, Zhengkun,Su, Zhengding,Zhang, Qian,Li, Dong
supporting information, p. 1193 - 1198 (2018/02/06)
A highly efficient copper-catalyzed C?H/N?H cross dehydrogenative coupling between picolinamides and simple ethers was developed. The reaction was promoted by the chelation assistance of removable picolinyl group and exhibited excellent TON and TOF number. This method was applicable to both N-aryl and alkyl picolinamides as well as various cyclic and acyclic ethers with good functional group compatibility. It also possessed the merit of air and moisture tolerance and easy operation. (Figure presented.).
The role of intermolecular interactions involving halogens in the supramolecular architecture of a series of Mn(II) coordination compounds
Khavasi, Hamid Reza,Ghanbarpour, Alireza,Tehrani, Alireza Azhdari
, p. 2422 - 2430 (2016/01/20)
A series of four new manganese(ii) complexes based on the L4-X ligand, where L is N-(4-halo)phenyl picolinamide ligands, have been synthesized, characterized and their supramolecular crystal structures were studied by geometrical analysis and t
Copper-catalyzed ortho-C-H amination of protected anilines with secondary amines
Martinez, Angel Manu,Rodriguez, Nuria,Arrayas, Ramon Gomez,Carretero, Juan C.
supporting information, p. 2801 - 2803 (2014/03/21)
A practical Cu-catalyzed picolinamide-directed o-amination of anilines showing excellent mono-substitution selectivity and high functional group tolerance has been developed.
