54758-74-6Relevant academic research and scientific papers
Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis
Paul, Amrita,Shah, Sk. Sheriff,Shee, Maniklal,Singh, Amit Kumar,Singh, N. D. Pradeep
supporting information, p. 3426 - 3439 (2020/03/23)
This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole. The applicability of this direct C-O bond formation method is shown by synthesizing several metal complexes of 2-(benzo[d]thiazol-2-yl)phenol that can be used in organic light-emitting diodes and pharmaceuticals.
Reusable Palladium Nanoparticles Catalyzed Oxime Ether Directed Mono Ortho-Hydroxylation under Phosphine Free Neutral Condition
Saha, Rajib,Perveen, Naziya,Nihesh, Naorem,Sekar, Govindasamy
supporting information, p. 510 - 519 (2018/12/11)
An efficient, reusable and stable binaphthyl stabilized Pd-nanoparticles (Pd-BNP) catalyzed the direct ortho-C?H hydroxylation of acetophenone oxime ethers under neutral and phosphine ligand-free condition has been developed. A readily available, economic, safe and greener oxidant oxone has been used in this direct ortho-hydroxylation. The scope of the reaction has been studied with various acetophenone oxime ethers including electron rich to electron deficient system and the reaction afforded only mono hydroxylated products in a highly regioselective manner. Several control experiment results confirmed that the oxone is the hydroxyl source. The Pd-BNP catalyst has been reused up to five times. The heterogeneous test confirmed that the reaction is catalyzed by the heterogeneous Pd-BNP catalyst. (Figure presented.).
Ruthenium(II)-Catalyzed Regioselective C-8 Hydroxylation of 1,2,3,4-Tetrahydroquinolines
Chen, Changjun,Pan, Yixiao,Zhao, Haoqiang,Xu, Xin,Luo, Zhenli,Cao, Lei,Xi, Siqi,Li, Huanrong,Xu, Lijin
supporting information, p. 6799 - 6803 (2018/11/21)
Ru(II)-catalyzed chelation-assisted highly regioselective C8-hydroxylation of 1,2,3,4-tretrahydroquinolines has been developed. Various 1,2,3,4-tetrahydroquinolines underwent smooth C8-H hydroxylation with cheap and safe K2S2O8 as the oxidant and oxygen source to furnish the corresponding products in good to excellent yields with high tolerance of the functional groups. The choice of a readily installable and removable N-pyrimidyl directing group is the key to catalysis. Mechanistic studies suggest the involvement of a six-membered ruthenacycle intermediate in the catalytic cycle. The method can also be extended to the direct hydroxylation of other (hetero)arene C-H bonds.
Ligand-Promoted Pd-Catalyzed Oxime Ether Directed C-H Hydroxylation of Arenes
Liang, Yu-Feng,Wang, Xiaoyang,Yuan, Yizhi,Liang, Yujie,Li, Xinyao,Jiao, Ning
, p. 6148 - 6152 (2015/10/12)
An efficient Pd-catalyzed oxime ether directed ortho C-H hydroxylation of arenes under neutral conditions has been developed. The efficiency of this hydroxylation is significantly improved by a ligand. Oxone, an inexpensive, readily available, and safe reagent, was employed as terminal oxidant and oxygen source. The challenging electron-deficient substrates could also be monohydroxylated in high efficiency. Drug modification with this protocol was also successfully demonstrated.
