33757-51-6Relevant academic research and scientific papers
Aryne Multicomponent Reactions by Directed C?H Activation
Sunnam, Sunil Kumar,Belani, Jitendra D.
, p. 8846 - 8850 (2021)
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.
Copper-Catalyzed Electrochemical Selective Bromination of 8-Aminoquinoline Amide Using NH4Br as the Brominating Reagent
Fang, Ping,Huang, Yan,Mei, Tian-Sheng,Wang, Xiang-Yang,Xu, Hao-Han,Yang, Qi-Liang,Yang, Xiang
, p. 3497 - 3507 (2020/03/23)
A simple and mild protocol for copper-catalyzed bromination of quinoline at the C5 site of quinoline by anodic oxidation was developed, affording the desired remote C-H activation products with isolated yields of up to about 90%. The reaction proceeds wit
Rhodium-Catalyzed Alkenylation of C-H Bonds in Aromatic Amides with Alkynes
Shibata, Kaname,Natsui, Satoko,Chatani, Naoto
supporting information, p. 2234 - 2237 (2017/05/12)
The rhodium-catalyzed alkenylation of C-H bonds of aromatic amides with alkynes is reported. A variety of functional groups, including OMe, OAc, Br, Cl, and even NO2, are applicable to this reaction to give the corresponding hydroarylation prod
Ligand-enabled, copper-promoted regio- and chemoselective hydroxylation of arenes, aryl halides, and aryl methyl ethers
Singh, Bijaya Kumar,Jana, Ranjan
, p. 831 - 841 (2016/02/18)
We report here a practical method for the ortho C-H hydroxylation of benzamides with inexpensive copper(II) acetate monohydrate and a pyridine ligand. An intra- and intermolecular ligand combination was explored to achieve regio- and chemoselective hydroxylation. Interestingly, typical regiochemical scrambling associated with the C-H activation was further resolved by introducing a ligand-directed ortho hydroxylation of haloarenes and aryl methyl ethers.
Copper(ii)-catalyzed C5 and C7 halogenation of quinolines using sodium halides under mild conditions
Xu, Jun,Zhu, Xiaolei,Zhou, Guobin,Ying, Beibei,Ye, Pingping,Su, Lingying,Shen, Chao,Zhang, Pengfei
, p. 3016 - 3021 (2016/03/19)
A simple and mild protocol for copper catalyzed halogenation of quinoline at C5 and C7 positions was developed, affording the desired remote C-H activation products in moderate to good yields. This reaction proceeds with low-cost sodium halides (NaX, X =
Copper-mediated ortho-nitration of arene and heteroarene c-h bonds assisted by an 8-aminoquinoline directing group
Liu, Jidan,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Yang, Zhiyong,Tan, Ze
supporting information, p. 732 - 738 (2015/03/18)
A copper-mediated, chelation-assisted ortho C-H bond nitration of benzoic acid derivatives using sodium nitrite as the source of the nitro group has been achieved with the aid of an 8-aminoquinoline directing group. Selective mono- or dinitration can be achieved by simply changing the reaction conditions. The method shows excellent functional group tolerance and provides a novel and straightforward route for the preparation of ortho-nitrated benzoic acids.
Copper-mediated ortho-nitration of (hetero)arenecarboxylates
Katayev, Dmitry,Pfister, Kai F.,Wendling, Timo,Goossen, Lukas J.
supporting information, p. 9902 - 9905 (2014/08/18)
Various (hetero)arenecarboxylic acids were converted to the corresponding Daugulis amides and nitrated selectively in the ortho-position in the presence of [CuNO3(PPh3)2] and AgNO2 at 50 °C. A microwave-assisted saponification allows regenerating the carboxylate group within minutes, which may then be removed tracelessly by protodecarboxylation, or substituted by aryl- or alkoxy-groups via decarboxylative cross-coupling.
