443647-45-8Relevant articles and documents
Aryne Multicomponent Reactions by Directed C?H Activation
Sunnam, Sunil Kumar,Belani, Jitendra D.
, p. 8846 - 8850 (2021/05/31)
Arylation via ortho C?H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C?H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C?H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C?H functionalization was observed when methylacrylate and acrylonitrile was added; this led to C?H olefination with the aryl group, which was installed from the aryne precursor.
Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides
Chen, Xi,Ding, Ya-Nan,Gou, Xue-Ya,Liang, Yong-Min,Luan, Yu-Yong,Niu, Zhi-Jie,Shi, Wei-Yu,Zhang, Zhe,Zheng, Nian
, p. 8945 - 8948 (2021/09/10)
C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.
C-H Amidation and Amination of Arenes and Heteroarenes with Amide and Amine using Cu-MnO as a Reusable Catalyst under Mild Conditions
Singh, Harshvardhan,Sen, Chiranjit,Suresh, Eringathodi,Panda, Asit B.,Ghosh, Subhash C.
, p. 3261 - 3275 (2021/02/16)
An atom-economical and efficient route for the direct amidation and amination of aryl C-H bonds using our synthesized recyclable heterogeneous Cu-MnO catalyst is reported here. The direct C-H amidation was carried out using a simple amide without any prea
C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane
Lin, Xinxin,Zeng, Cuilian,Liu, Chengkou,Fang, Zheng,Guo, Kai
supporting information, p. 1352 - 1357 (2021/02/26)
An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale
Metal-Free Electrochemical Oxidative Dihalogenation of Quinolines on the C5 and C7 Positions Using N-Halosuccinimides
Hou, Jiahao,Wang, Kai,Zhang, Changjun,Wei, Tingting,Bai, Renren,Xie, Yuanyuan
supporting information, p. 6382 - 6386 (2020/10/19)
An efficient and convenient method for electrochemically oxidative dichlorination or dibromination of 8-aminoquinolines on C5 and C7 positions using N-halosuccinimides (NCS and NBS) as the halogen source was described. Substrates with various functional g
Catalyst- And oxidant-free electrochemical: para -selective hydroxylation of N -arylamides in batch and continuous-flow
Chen, Meng-Yi,Fang, Zheng,Guo, Kai,Lin, Xin-Xin,Liu, Cheng-Kou
supporting information, p. 6437 - 6443 (2020/11/09)
Hydroxyl compounds serve as key building blocks in the preparation of biologically active natural products and drugs. Traditionally, hydroxylation of the aromatic ring is achieved using stoichiometric amounts of oxidants, which leads to low atom-economy, undesired by-products, potential explosion risk and environmental pollution. Recently, electrosynthesis has attracted increasing attention as it employs clean electrical energy to promote redox reactions avoiding the use of oxidants. However, due to the poor mass and heat transfers of batch cells, low productivity and selectivity limit its further application. Herein, we develop a catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at room temperature in batch and continuous-flow. This proposal features excellent position control and water, air and functional group tolerance. Also, it is easy to scale up with higher productivity and selectivity using a flow electrolysis cell.
Copper-Catalyzed C-4 Carboxylation of 1-Naphthylamide Derivatives with CBr4/MeOH
Sahoo, Tapan,Sen, Chiranjit,Singh, Harshvardhan,Suresh,Ghosh, Subhash Chandra
supporting information, p. 3950 - 3957 (2019/07/19)
A simple and practical copper catalyzed C-4 carboxylation reaction of 1-naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4-H functi
Electrooxidative amination of sp2 C-H bonds: Coupling of amines with aryl amides via copper catalysis
Kathiravan, Subban,Suriyanarayanan, Subramanian,Nicholls, Ian A.
, p. 1968 - 1972 (2019/03/07)
Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis. However, the use of C-H activation for sp2 C-N bond formation remains one of the major challenges in the field of cross-coupling chemistry. Described herein is the first example of the synergistic combination of copper catalysis and electrocatalysis for aryl C-H amination under mild reaction conditions in an atom-and step-economical manner with the liberation of H2 as the sole and benign byproduct.
Rhodium-Catalyzed Alkylation of C?H Bonds in Aromatic Amides with Non-activated 1-Alkenes: The Possible Generation of Carbene Intermediates from Alkenes
Yamaguchi, Takuma,Natsui, Satoko,Shibata, Kaname,Yamazaki, Ken,Rej, Supriya,Ano, Yusuke,Chatani, Naoto
, p. 6915 - 6919 (2019/05/10)
The alkylation of C?H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C?H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.
Copper-mediated synthesis of quinazolin-4(3: H)-ones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides
Ban, Zihui,Cui, Xinfeng,Hu, Fangpeng,Lu, Guoqiang,Luo, Nan,Huang, Guosheng
supporting information, p. 12963 - 12966 (2019/08/28)
An efficient copper-mediated tandem C(sp2)-H amination to provide quinazolinones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides has been developed. It can afford rather complex products in a single step synthesis from easily availab
