796068-66-1Relevant academic research and scientific papers
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
Copper-Catalyzed Electrophilic Ortho C(sp2)-H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System
Begam, Hasina Mamataj,Choudhury, Rajarshee,Behera, Ashok,Jana, Ranjan
supporting information, p. 4651 - 4656 (2019/06/17)
A practical copper-catalyzed, 2-picolinamide-directed ortho C-H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, b
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.
Experimental and mechanistic insights into copper(ii)-dioxygen catalyzed oxidative: N -dealkylation of N -(2-pyridylmethyl)phenylamine and its derivatives
Wang, Yang,Liu, Haixiong,Zhang, Xiaofeng,Zhang, Zilong,Huang, Deguang
, p. 9164 - 9168 (2017/11/15)
A di-(2-pyridylmethyl)phenylamine ((PyCH2)2NPh) supported Cu(ii)/O2 catalytic system was explored with the synthesis of pyridylmethyl-based compounds of carboxylate (PyCOOH), amide (PyC(O)NHPh), and imine (PyCHNPh) from the oxidative N-dealkylation of N-(2-pyridylmethyl)phenylamine (PyCH2NHPh) and its derivatives, by means of controlling the addition of a base and/or water to the reaction system under a dioxygen atmosphere at room temperature. Experimental studies showed that the imine and amide species could be precursors in succession in the way to the final oxidation state of carboxylates. A cyclic catalytic mechanism was proposed including the base triggered C-H bond activation of the 2-pyridylmethyl group (PyCH2-) and the intermolecular Cu-OOH α-hydrogen atom abstraction from the coordinated imine substrate (PyCHNPh).
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 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.
