312503-18-7Relevant articles and documents
Copper(II)-Mediated Intermolecular C(sp2)-H Amination of Benzamides with Electron-Rich Anilines
Singh, Bijaya Kumar,Polley, Arghya,Jana, Ranjan
, p. 4295 - 4303 (2016)
Despite significant progress, copper-catalyzed/mediated C-H amination reactions with electron-rich anilines remain an unsolved problem due to catalyst deactivation and deleterious side reactions. Herein, we report a copper(II)-mediated C(sp2)-H amination of benzamides with electronically neutral or electron-rich anilines. A dramatic influence of silver(I) and tetrabutylammonium bromide was observed on the reaction outcome. The present protocol also demonstrates the synthesis of a number of nonsteroidal anti-inflammatory drugs.
Copper-Catalyzed Direct Acyloxylation of C(sp2)-H Bonds in Aromatic Amides
Wang, Feifan,Hu, Qiyan,Shu, Chao,Lin, Zhiyang,Min, Dewen,Shi, Tianchao,Zhang, Wu
, p. 3636 - 3639 (2017)
Copper-catalyzed ortho-acyloxylation of the sp2 C-H bond of aryl amides with carboxylic acids is reported. Benzoic acids, cinnamic acids, and aliphatic acids can be involved, and the desired products were obtained in moderate to good yields. This procedure is compatible with a wide range of functional groups and heteroarenes without the use of any ligands or additives. This method provides an operationally simple approach for the synthesis of benzoate and cinnamate.
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.
Divergent copper-mediated dimerization and hydroxylation of benzamides involving C-H bond functionalization
Wang, Mingliang,Hu, Yimin,Jiang, Zhe,Shen, Hong C.,Sun, Xun
, p. 4239 - 4246 (2016/05/24)
Convenient methods were developed for copper-mediated oxidative C-H activation of aminoquinoline benzamides. The reaction conditions can be tuned to give either hydroxylation or dimerization compounds as the major products efficiently. Preliminary mechanistic studies suggested that different coordination states of copper may lead to different reaction outcomes.
Copper-/Silver-Mediated Arylation of C(sp2)-H Bonds with 2-Thiophenecarboxylic Acids
Zhao, Sheng,Liu, Yue-Jin,Yan, Sheng-Yi,Chen, Fa-Jie,Zhang, Zhuo-Zhuo,Shi, Bing-Feng
supporting information, p. 3338 - 3341 (2015/07/08)
A copper/silver-mediated arylation of (hetero)aryl C-H bonds with 2-thiophenecarboxylic acids has been achieved. The protocol features a broad substrate scope and high functional group tolerance. Preliminary mechanistic studies indicate that a cascade pro
Copper-mediated hydroxylation of arenes and heteroarenes directed by a removable bidentate auxiliary
Li, Xin,Liu, Yan-Hua,Gu, Wen-Jia,Li, Bo,Chen, Fa-Jie,Shi, Bing-Feng
supporting information, p. 3904 - 3907 (2014/08/18)
A copper-mediated C-H hydroxylation of arenes and heteroarenes using our newly developed PIP directing group has been developed. This procedure is scalable and compatible with a wide range of functional groups and heteroarenes, providing an operationally simple protocol for the synthesis of o-hydroxybenzamides. The hydroxylation of nicotinamides gave 4-oxo-1,4-dihydropyridine-3-carboxamides selectively. Preliminary mechanistic studies implicate that a basic ligand-enabled, irreversible, rate-determining CMD step is most likely involved in this process.
