Article
Chemistry, Organic
Zhiguang Zhang, Xiaojie Lan, Xiaomin Zhang, Yanmei Liu, Jinxin Gao, Bingzhu Zhang, Haixia Wu
Summary: Herein, we introduce a practical protocol for synthesizing symmetrical disulfides under atmospheric pressure using 1 mol% ABNO (9-Azabicyclo[3.3.1]nonane N-oxyl) as an efficient catalyst and O-2 as a terminal oxidant. Both thiophenols and aliphatic thiols could be smoothly oxidized to yield disulfides in yields of 70%-90%. This method offers advantages such as high atom-economy, commercially available catalyst, broad substrate scope, and mild reaction conditions, providing researchers a simple and attractive way to synthesize disulfides.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jordan E. Nutting, Kaining Mao, Shannon S. Stahl
Summary: The study reveals different mechanistic differences between Cu/aminoxyl and Fe/aminoxyl catalyst systems, leading to distinct alcohol oxidation chemoselectivity and functional group compatibility. The Fe/aminoxyl system involves a redox cascade reaction, while the Cu/aminoxyl system exhibits integrated cooperativity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Wei Zhong, Jiabin Luo, Zhenzhen Liu, Guangli Zhan, Lihua Zhu, Chunxin Lu, Zhongquan Shen, Xueming Li, Xiaoming Liu
Summary: This study investigated the mechanistic aspects of CuI-catalyzed aerobic oxidation of alcohols using N,N,N',N'-tetramethylethylenediamine (TMEDA) as a ligand and 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) as a co-catalyst. The system exhibited excellent catalytic activity for selective oxidation of primary alcohols, yielding quantitative results on a preparative scale. Through mechanistic investigation, two binuclear copper complexes (1 and 2) were isolated, with 1 being an intermediate in the catalytic cycle initiated by CuI. However, an independent catalytic pathway was observed for complex 2, which maintained its dinuclear integrity throughout the process.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Kamaless Patra, Arindom Bhattacherya, Chenfei Li, Jitendra K. Bera, Han Sen Soo
Summary: In this study, a photocatalytic synthesis method using visible light as the driving force was proposed for the synthesis of quinolines and naphthyridines under ambient and aerobic conditions. The method demonstrated a broad substrate scope and applicability for the synthesis of pharmaceutical ingredients and natural products.
Article
Chemistry, Organic
Guo-Qing Jiang, Bin-Hong Han, Xian-Peng Cai, Jian-Ping Qu, Yan-Biao Kang
Summary: An iron-catalyzed direct aerobic alpha,beta-dehydrogenation of carbonyls has been reported using tert-butyl nitrite and N-hydroxyphthalimide as the co-catalyst system. This method allows for the production of a wide range of lactams, flavanones, lactone, and thiochromen-4-one in high yields without the need for extra transition metal reagents.
Article
Chemistry, Physical
Yunlian Yang, Wei Zhong, Ruonan Ma, Chunxin Lu, Zhongquan Shen, Xiaoming Liu, Shuhua Zhang, Hongming Wang
Summary: The study transformed cuprous oxide into an efficient catalyst for the aerobic oxidation of benzylic alcohols to aldehydes under ambient conditions through surface coordination with TEMPO and NMI. The coordination enhanced O-2 activation capability and engineered the surface structure to allow O-2-binding, as shown by experimental and theoretical results.
APPLIED SURFACE SCIENCE
(2021)
Article
Chemistry, Organic
Dustin D. Youmans, Hai N. Tran, Levi M. Stanley
Summary: Nickel-catalyzed isomerizations of homoallylic alcohols and a bishomoallylic alcohol proceed efficiently without the need for an exogenous ligand. The corresponding ketones are obtained in high yields (≤98%).
Article
Chemistry, Multidisciplinary
Srimanta Manna, Wei-Jun Kong, Jan-E Backvall
Summary: This study presents an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions, inspired by oxidations in the respiratory chain. The method utilizes environmentally friendly and inexpensive catalysts, delivering important heterocycles in good-to-excellent yields with a broad substrate scope.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Man Wang, Rui Wang, Long Zhang, Wen Si, Ran Song, Daoshan Yang, Jian Lv
Summary: An efficient solvent-free radical oxyamination reaction has been demonstrated for the modification of carbonyl compounds adjacent to different chalcogens (e.g., S, O, and Se). This method does not require the use of a transition metal catalyst, chemical oxidant, or photocatalyst, and exhibits a wide substrate scope and high functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jin Bai, Sijia Yan, Zhuxia Zhang, Zhen Guo, Cong-Ying Zhou
Summary: A metal-free heterogeneous photocatalysis using inexpensive graphitic carbon nitride (g-C3N4) has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides under visible-light irradiation. This reaction provides high yields of 2-substituted benzothiazoles without the need for a strong base or organic oxidizing reagents, and the catalyst is stable and reusable after five reaction cycles.
Article
Chemistry, Multidisciplinary
Qi Zhao, Yongtao Wang, Yu Wang, Qixuan Hu, Jia Yao, Zeyu Wen, Haoran Li
Summary: The main product from keto acid to alpha-hydroxyl ketone can be effectively controlled by reducing the concentration of FeCl3 catalyst and using DMSO as the solvent. Mechanistic investigations indicate that the same FeCl3-coordinated peroxide intermediate plays a role in both hydroxylation and C-C cleavage routes, and emphasize the role of DMSO as both ligand and reductant. This work provides a new approach for selective aerobic oxidation under Lewis acid catalysis.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Meng Guan, Ming Hou, Shuwang Tang, Guang Cheng, Xinyu Zhu, Yun-Hui Zhao, Ximei Tang, Hongwei Zhou, Guanyinsheng Qiu
Summary: This study describes the synthesis of various drug-like molecules and natural product through an iron-catalyzed divergent oxidation reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Yongke Hu, Lei Chen, Gulou Shen, Jin Li, Shaozhong Li, Huaju Li, Yanxing Li
Summary: An efficient catalytic system for the oxidation of alcohols to aldehydes/ketones has been developed, using catalytic amounts of Bi(NO3)(3) and Keto-ABNO with air as the oxidant. Various alcohols were smoothly oxidized to the corresponding products under mild conditions, achieving satisfactory yields without the use of a ligand or base.
Article
Chemistry, Organic
Nicolas Joly, Leo Bettoni, Sylvain Gaillard, Albert Poater, Jean-Luc Renaud
Summary: In this study, a new synthesis method for mono- or dialkylated acyl hydrazide compounds was developed using a diaminocyclopentadienone ruthenium tricarbonyl complex-catalyzed borrowing hydrogen strategy with various substituted primary and secondary alcohols as alkylating reagents. Experimental results confirmed that alcohols were the hydrogen source, and density functional theory (DFT) calculations revealed the differences between mono- and dialkylation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daisuke Uraguchi, Kohsuke Kato, Takashi Ooi
Summary: An o-quinone methide (o-QM) with an overcrowded olefinic framework is introduced, showing dehydridation activity due to its enhanced zwitterionic character, especially under photoexcitation. Experimental analysis and density functional theory calculations provide mechanistic insights, revealing that the o-QM operates in dehydridative catalysis for the oxidation of benzylic secondary alcohols.
