Article
Chemistry, Organic
Hong Xin, Xin-Hua Duan, Mingyu Yang, Yiwen Zhang, Li-Na Guo
Summary: A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been successfully demonstrated, leading to the formation of distal keto acids or dicarboxylic acids with moderate to good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Katrin Warm, Guilherme Tripodi, Erik Andris, Stefan Mebs, Uwe Kuhlmann, Holger Dau, Peter Hildebrandt, Jana Roithova, Kallol Ray
Summary: The Cu-I/TEMPO catalyst system has been shown to selectively yield aldehydes in aerobic alcohol oxidation reactions. By detecting reactive intermediates and conducting kinetic studies, the mechanisms of O-2 reduction and alcohol oxidation reactions have been clarified. This study provides valuable insights into the aerobic oxidation of alcohols and transition-metal catalysts involving redox-active organic cocatalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Divya Bhatt, Hun Young Kim, Kyungsoo Oh
Summary: In this study, the synthesis of 3-sulfonyl furans was achieved by the addition of sodium sulfinate to (E)-beta-chlorovinyl ketones, followed by the aerobic cyclization of alkenyl sulfone intermediates. The optimal catalyst system for the cyclization was identified as Cu(OTf)(2), with molecular oxygen as the terminal oxidant. This strategy allows the synthesis of highly functionalized and substituted furan derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Arsala Kamal, Himanshu Kumar Singh, Dhirendra Kumar, Suresh Kumar Maury, Savita Kumari, Vandana Srivastava, Sundaram Singh
Summary: The methodology is environmentally friendly, mild, and allows for a wide range of functional groups with good tolerance. It is cost-effective, has high atom economy, short reaction time, and is applicable for large-scale synthesis.
Article
Chemistry, Physical
Yu Li, Guo-Cui Ji, Chen Chao, Siwei Bi, Yuan-Ye Jiang
Summary: This study investigates the mechanism of Cu-catalyzed aerobic aminooxygenation of alkene-tethered amides through computational analysis. The results reveal that Cu(I) precursor is not the active species and the reaction is initiated by the formation of Cu(II) complexes. The study contributes to the understanding of Cu-catalyzed aerobic reactions.
Article
Chemistry, Organic
Raghunath Chowdhury
Summary: Catalytic aerobic oxidative coupling reactions of glycine esters with various substrates were achieved at low temperature using the ground state reactivity of eosin-Y. This method allows the synthesis of structurally diverse unnatural amino acid derivatives and offers advantages such as step economy, broad substrate scope, and operational simplicity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Weiqiang Sun, Xueli Cui, Jing Qu, Xiaojia Cai, Jinhui Hu, Zhuang Xiong, Suqin Guo, Jun Xu, Wen-Hua Chen, Jia-Qiang Wu
Summary: This paper presents a practical and versatile oxidative cyclization reaction of 2-arylethynylanilines to form 2-hydroxy-2-substituted indol-3-ones using a copper-catalyzed radical approach in the presence of O-2. The transformation of 2-hydroxy-2-arylindol-3-ones to 3-hydroxy-3-arylindol-2-ones is efficient and demonstrates the practicality and utility of this catalytic system. Mechanistic investigations revealed that the acetyl substituent on 2-arylaethynylanilines plays a crucial role in the formation of the cyclic products through an N-center radical-based 5-endo-dig aza-cyclization pathway.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Yu Li, Guo-Cui Ji, Chen Chao, Siwei Bi, Yuan-Ye Jiang
Summary: This article reports a computational study on the mechanism of Cu-catalyzed aerobic aminooxygenation reactions. It was found that a Cu(I) precursor can generate two types of Cu(II) complexes to initiate the reactions. The first catalytic stage involves the conversion of alkene-tethered amides to alpha-amidated aldehydes, while the second stage involves the generation of imides from alpha-amidated aldehydes. The presented findings expand our understanding of Cu-catalyzed aerobic reactions and the role of different copper complexes.
Article
Chemistry, Physical
Yi-Ting Tsai, Jia-Liang Zhu
Summary: Several types of 2-diazo-1,3-dicarbonyl compounds can be transformed into vicinal tricarbonyls through aerobic oxygenation with Rh2(OAc)4 catalyst and oxygen gas. The reaction is facilitated by weak interaction with the substrate carbonyl group and suppresses the Wolff rearrangement. The isolated yields of the desired products range from 27% to 92%, depending on the starting materials.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Kaikai Niu, Xiaodi Shi, Ling Ding, Yuxiu Liu, Hongjian Song, Qingmin Wang
Summary: A practical chlorine radical-mediated aerobic oxidation method for converting alkylarenes to carbonyls was developed in this study. This strategy utilized HCl as a hydrogen atom transfer reagent and air as a sustainable oxidant, showing excellent functional group tolerance and a broad substrate scope without the need for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, O-18 labeling, and control experiments.
Review
Chemistry, Organic
Hun Young Kim, Kyungsoo Oh
Summary: This review highlights the interplay between copper catalysts and molecular oxygen in controlling aerobic C-sp(3)-H bond oxidations. Specifically, it focuses on the Cu-catalyzed oxidations of benzylic, alpha-carbonyl, and amine group adjacent carbons over the past five years. Furthermore, discussion on the development of tandem multicomponent reactions utilizing aerobic C-sp(3)-H bond oxidations underscores the importance of controlled catalyst behaviors and interactions between multiple reaction components.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Le Anh Nguyen, Thi Thu Tram Nguyen, Quoc Anh Ngo, Thanh Binh Nguyen
Summary: A Fe/S catalyst generated in situ from FeCl2•4H2O and elemental sulfur S-8 in the presence of a tertiary amine efficiently catalyzed a 6e(-) redox condensation of o-nitrophenols with acetophenones and methylquinolines, giving reasonable yields of condensed products 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles with water as the sole byproduct at a low temperature of 80 degrees C.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Asit Kumar Das, Sneha Nandy, Sanjay Bhar
Summary: An economically efficient and environmentally benign method for the direct oxidative transformation of aldehydes to nitriles has been developed. The reaction showed high yield and good tolerance towards various sensitive moieties. The method also demonstrated potential for industrial application.
Article
Chemistry, Multidisciplinary
Andrea N. Blankenship, Manoj Ravi, Mark A. Newton, Jeroen A. van Bokhoven
Summary: An efficient strategy for direct methane conversion involves protecting methanol by esterification to a more stable methyl ester. A new approach using a dispersed cobalt catalyst shows improved reaction conditions and competitive yields compared to traditional homogeneous catalytic methods. This method also utilizes a specific solvent system for product separation and recovery, enhancing overall efficiency.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Zi-Chen Wang, Rui-Tao Li, Qiang Ma, Jia-Yi Chen, Shao-Fei Ni, Ming Li, Li-Rong Wen, Lin-Bao Zhang
Summary: A method for electrochemically driven Rh(iii)-catalyzed regioselective annulation of arenes with alkynes has been established, which avoids the use of external oxidant, proceeds under mild and green conditions, and is compatible with a broad range of substrates including drugs. This method is operationally simple and efficient in aqueous solution in air.
