Review
Chemistry, Organic
Yan Boyu, Wu Jieliang, Deng Jinfei, Chen Dan, Ye Xiushen, Yao Qiuli
Summary: This review covers recent progress in the light-driven direct deoxygenation of alcohols, with emphasis on important advances in the past decade, which is expected to further promote the rapid development in this field.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaobo Pang, Xing-Zhong Shu
Summary: This perspective manuscript summarizes the recent advances in radical dehydroxylative transformation of alcohols either promoted or catalyzed by titanium, highlighting the potential of low-valent titanium in producing carbon radicals from alcohols. The limitations and future prospects in this field are also discussed.
Article
Chemistry, Organic
Valeriy O. Filimonov, Alexandra I. Topchiy, Vladimir G. Ilkin, Tetyana V. Beryozkina, Vasiliy A. Bakulev
Summary: It was found that the reaction between 2-cyanothioacetamides and hydrazine involves both cyano and thioamide groups, resulting in the formation of 3,5-diaminopyrazoles. Meanwhile, in the reaction of 2-cyano-3-(dimethylamino)-N,N-dimethylprop-2-enethioamides with hydrazine and its derivatives, cyano and enamine groups participate in the reaction without affecting the thiocarbamoyl group, leading to the synthesis of 4-thiocarbamoylpyrazoles. A synthesis method for 1-substituted-4-thiocarbamoyl pyrazoles has been developed, and the structure of the reaction products has been confirmed using NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Inorganic & Nuclear
Yuhuan Qin, Mingming Hao, Dengke Wang, Zhaohui Li
Summary: Utilizing solar energy through photocatalysis is a promising strategy for addressing energy shortages and environmental issues. Metal-organic frameworks (MOFs) are emerging as a new type of photocatalytic material, with post-synthetic modifications (PSM) being a powerful strategy for fabricating photoactive MOFs based on existing MOFs. Various PSM strategies, including coordination on unsaturated metal sites, metalation on open coordinated sites, and ligand exchange, have been summarized for the development of photoactive MOFs.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Ling Luo, Jin-Hong Lin, Ji-Chang Xiao
Summary: A Ph3P/ICH2CH2I-promoted dehydroxylative cyanation of alcohols has been developed, which offers convenient operations, mild reaction conditions, and the use of cheap and widely available reagents, avoiding the limitations of previous methods that involve transition metals or moisture-sensitive Lewis acids.
Review
Chemistry, Inorganic & Nuclear
Andrey Y. Khalimon
Summary: Deoxygenative reduction of amides is a challenging task due to the low electrophilicity of the amide carbonyl group. Previously, efforts focused on hydrogenation and hydrosilylation approaches, which had limitations in terms of selectivity. On the other hand, deoxygenative hydroboration of amides has shown advantages in terms of scope, conditions, and selectivity compared to traditional methods.
DALTON TRANSACTIONS
(2021)
Review
Chemistry, Organic
Rajnish Kumar, Himanshu Singh, Avijit Mazumder, Salahuddin, Ranjeet Kumar Yadav
Summary: The pyrazoline moiety is widely used in pharmaceutical, agricultural, and industrial sectors, and its chemistry has been extensively studied. Various synthesis strategies have been developed, but researchers are continuously exploring greener and more economical methods.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Christopher J. J. Hall, William R. F. Goundry, Timothy J. Donohoe
Summary: Enantiopure 1,2-amino alcohols derived from abundant amino acids were used in C-C bond-forming hydrogen-borrowing alkylation reactions for the first time. The use of Ph*COMe aryl ketone facilitated the reactions, preventing racemisation of the amine stereocentre. The Ph* and trityl groups could be easily cleaved in one pot to give GABA products without further purification, allowing the two steps to be performed in sequence without isolation of the hydrogen-borrowing intermediate, eliminating the need for column chromatography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Physical
Pengyi Lu, Jingwen Zhou, Yukun Hu, Jinwen Yin, Yunhao Wang, Jinli Yu, Yangbo Ma, Zonglong Zhu, Zhiyuan Zeng, Zhanxi Fan
Summary: Gold-based nanoalloys have garnered extensive attention for their intriguing physical/chemical properties and excellent performance in various applications, particularly in catalysis. This review provides an overview of general synthetic methods and potential catalytic applications of gold-based nanoalloys, as well as discusses the relationships between material structures/compositions and catalytic performances. Additionally, critical challenges and potential opportunities facing gold-based nanoalloys are proposed to inspire future material design for high performance applications.
JOURNAL OF MATERIALS CHEMISTRY A
(2021)
Article
Chemistry, Multidisciplinary
Mitsuki Onoda, Ken-ichi Fujita
Summary: Esters and ethers are commonly used compounds in modern organic synthesis. The dehydrogenative coupling of primary alcohols for ester synthesis has recently been proposed as an environmentally friendly process. In this study, a new catalytic function switching system was successfully developed using a single iridium catalyst, enabling both dehydrogenative esterification and dehydrative etherification under environmentally friendly conditions.
Review
Chemistry, Organic
Phuc H. Pham, Haley A. Petersen, Jaclyn L. Katsirubas, Oana R. Luca
Summary: This paper summarizes recent advances in mediated electrochemical and photoelectrochemical bond activation, including C-H, C-C, C-N, and other C-heteroatom bonds, driven by a resurgence of interest in electrode-driven synthetic methods.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Physical
Ashwani Kumar, Mitchell D. Nothling, Heather M. Aitken, Zeyun Xiao, Matthew Lam, Craig A. Bell, Megan L. O'Mara, Luke A. Connal
Summary: Inspired by the chemical structure of chymotrypsin, an artificial catalytic triad with high catalytic efficiency for the transesterification reaction of vinyl trifluoroacetate and methanol was developed. The addition of a hydrophobic chain allowed the formation of amphiphilic catalysts, which formed clusters for reactions in organic solvents. Molecular dynamics simulations, dynamic light scattering, and H-1 NMR revealed complex H-bonding interactions between the catalytic head groups of the artificial catalytic triad, resembling native enzymes.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Nicholas M. Wang, Sam Dillon, Damien Guironnet
Summary: A mechanistic investigation on ethanol self-condensation reaction catalyzed by a Ru(ii) catalyst was conducted in a specifically designed CSTR. The catalyst's activity was monitored using an in-line gas chromatograph, indicating good reactivity towards butanol and fast hydrogenation.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Christian Frabitore, Jerome Lepeule, Bradley Towey, Tom Livinghouse, William C. Robinson
Summary: The study showed that primary amine borane complexes are highly effective in reducing N,N-dimethylhydrazones, yielding the corresponding air-sensitive hydrazine products in excellent yields with as little as 1.1 equivalents.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Debabrat Pathak, Bikash Kumar Kalita, Ashish Sarmah, Himanshu Sharma, Bidisha Bora, Tridib K. Goswami, Bipul Sarma
Summary: We present a greener synthetic route for the synthesis of medicinally and industrially valuable quinoline scaffolds, eliminating harsh reaction conditions, low productivity, and unstable substrates associated with classical methods. This route involves the acceptorless dehydrogenative annulation of readily available alcohols in basic media using an engineered nitrogen-rich hollow-spherical microporous polymer (MOP-TA) without any metal support. The scalability and green matrices of this affordable and sustainable route are supported by various spectroscopic and microscopic techniques.
Article
Fisheries
Yingrui Li, Lin Su, Baoshan Guo, Shun Zhou, Chao Li, Yunji Xiu
Summary: Pathogens infection induces intestinal inflammatory processes. MicroRNAs in teleost serve as vital regulators in innate immunity responses against pathogen infection. MiR-144-5p is identified as negative regulator in teleost against bacterial infection. It down-regulates inflammation-related cytokines by targeting Hsp90 alpha, ultimately promoting bacterial infection.
Article
Fisheries
Hui Jun Huo, Tian Zhen Yang, Qing Zhu, Ning Yang, Chao Li
Summary: This study compared collectins from a range of vertebrates and found that they are widely distributed and conserved. The collectin from a marine teleost, the black rockfish, was analyzed in detail, revealing the need for further research on its sugar binding mechanism.
Article
Engineering, Environmental
Dandan Liang, Zeng Li, Guohong Liu, Chao Li, Weihua He, Jiannan Li, Yujie Feng
Summary: Periodic polarity reversal strategy can effectively cultivate bidirectional electron transfer biofilm and utilize the characteristics of biofilm to facilitate nitrate reduction.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Fisheries
Min Cao, Qi Li, Xiantong Liu, Qiang Fu, Chao Li
Summary: Sebastes schlegelii is a fish species with high economic value, but the outbreak of diseases in its aquaculture industry has caused significant economic losses. Study of the fish immune system, particularly the immunoglobulin genes, can provide insights into the immune response to pathogens and contribute to the development of prevention and control methods. This study successfully identified and cloned the immunoglobulin heavy chain genes (sIgM, mIgM, sIgT, and mIgT) of S. schlegelii, revealing their high conservation during evolution.
FISH & SHELLFISH IMMUNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Jianjin Yu, Renqin Zhan, Chao-Jun Li, Huiying Zeng
Summary: In this study, iodomethane was used as a C1 organocatalyst for the aerobic ortho-selective trifluoromethylation of pyridines without a transition metal. Trifluoroacetic acid was employed as an affordable and readily available trifluoromethyl source. The reaction showed good functional group compatibility and could selectively trifluoromethylate pyridine-containing drug molecules for late-stage functionalizations.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Juan D. D. Lasso, Durbis J. J. Castillo-Pazos, Malcolm Sim, Joaquin Barroso-Flores, Chao-Jun Li
Summary: Despite being well-known for their photochemical properties and industrial value, the use of nitroarenes as a productive photochemical handle in organic synthesis has been relatively unexplored. In this study, we report the design and application of a sulfinate-nitroarene electron donor-acceptor (EDA) complex, which enabled the first light mediated catalyst-free synthesis of N-hydroxy-sulfonamides. The EDA complex was characterized spectroscopically and studied using DFT and TD-DFT calculations. A total of 32 examples with electron withdrawing and electron donating groups were synthesized under oxygen- and water-tolerant conditions.
Article
Chemistry, Organic
Jiaxin Yao, Lin Yu, Wengui Duan, Chao-Jun Li
Summary: This study developed a novel method for the synthesis of arylsilane via Pd-catalyzed cross-coupling of hexamethyldisilane with nitroarenes. The method exhibits high selectivity and utilizes readily accessible chemical feedstocks.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Chengbin Gao, Xin Cai, Le Ma, Ting Xue, Chao Li
Summary: In this study, the TNF alpha was characterized and its roles in the immune system of black rockfish during bacterial infections were explored. The results showed that Ss_TNF alpha was significantly up-regulated in the spleen and intestine after infections, while down-regulated in PBLs. The expression patterns of other inflammatory cytokines were also observed.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Pediatrics
Mei Mei, Dan Dai, Zhuoyao Guo, Congcong Zhang, Jing Liu, Yuanyuan Qi, Xiaochuan Wang, Libo Wang, Liling Qian
Summary: This study retrospectively analyzed the clinical characteristics and underlying causes of 551 hospitalized children with recurrent pneumonia from January 2016 to January 2021 at the Children's Hospital of Fudan University. The majority (87.7%) of the children had underlying causes, with recurrent aspiration, primary immunodeficiency, and congenital heart diseases being the most common. Genetic defects were identified in about a quarter of the patients. Primary immunodeficiency, primary ciliary dyskinesia, bronchiolitis obliterans, and the age of >3 years at diagnosis were risk factors for severe outcomes. Aspiration and an abnormal family history were risk factors for rehospitalization.
PEDIATRIC PULMONOLOGY
(2023)
Article
Endocrinology & Metabolism
Peng Wang, Haifeng Sun, Gulisudumu Maitiabula, Li Zhang, Jianbo Yang, Yupeng Zhang, Xuejin Gao, Jieshou Li, Bin Xue, Chao-Jun Li, Xinying Wang
Summary: Total parenteral nutrition (TPN) can cause glucose metabolism disorders by altering the gut microbiota and its metabolites, leading to insulin resistance and an increased risk of complications. Decreased levels of Lactobacillaceae and indole-3-acetic acid (IAA) are associated with these complications, while the abundance of Lactobacillaceae and IAA is negatively correlated with insulin resistance and serum lipopolysaccharide levels. IAA activates the aryl hydrocarbon receptor and increases glucagon-like peptide-1 secretion, preventing TPN-induced glucose metabolism disorders in mice.
Article
Chemistry, Multidisciplinary
Hyotaik Kang, Lida Tan, Jing-Tan Han, Chia-Yu Huang, Hui Su, Aleksei Kavun, Chao-Jun Li
Summary: We demonstrate the use of gallium nitride (GaN) as a non-toxic, recyclable, heterogeneous photocatalyst in conjunction with the catalytic use of benzophenone to activate alkyl C(sp(3))-H bonds and generate alkyl radicals. This dual photocatalytic cycle enables cross-dehydrogenative Minisci alkylation under mild and chemical oxidant-free conditions.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Organic
Yi-Zhan Wang, Shao-Dong Liu, Liang Cheng, Li Liu, Chao-Jun Li
Summary: An asymmetric umpolung addition of hydrazones as alkyl carbanion equivalents with imines in water was developed using a Ru-diamine-diphosphine system in the presence of crown ether. Chiral amines were obtained in moderate to good yields with high enantioselectivities. The use of water as a reaction medium provided better yields and enantioselectivities compared to organic solvents, offering a new method for the green and sustainable synthesis of chiral amines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Cell Biology
Chuanming Liu, Wu Zuo, Guijun Yan, Shanshan Wang, Simin Sun, Shiyuan Li, Xinyi Tang, Yifan Li, Changjun Cai, Haiquan Wang, Wenwen Liu, Junshun Fang, Yang Zhang, Jidong Zhou, Xin Zhen, Tianxiang Feng, Yali Hu, Zhenbo Wang, Chaojun Li, Qian Bian, Haixiang Sun, Lijun Ding
Summary: With aging, abnormalities during oocyte meiosis become more prevalent, and the mechanisms of aging-related oocyte aneuploidy are not fully understood. This study reveals that disruptions in the mevalonate (MVA) pathway in granulosa cells (GCs) contribute to meiotic defects and aneuploidy in oocytes. Supplementation with MVA metabolites improves oocyte quality, suggesting a potential therapeutic strategy for promoting female reproductive longevity.
Article
Chemistry, Organic
Ruohua Gui, Chao-Jun Li
Summary: Historically, deuteration reactions were mainly used for mechanistic studies, but their pharmacological importance is now recognized. Efforts have been made to meet the urgent need for deuteration tools since the approval of the first deuterated drug for Huntington's disease. Current deuteration strategies involving reversible H/D exchange have limitations in functional group tolerance and deuterium content. In this study, a ruthenium-catalyzed deoxygenative deuteration of ketones was developed, allowing regiospecific deuteration with high deuterium content.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Durbis J. Castillo-Pazos, Juan D. Lasso, Ehsan Hamzehpoor, Jorge Ramos-Sanchez, Jan Michael Salgado, Gonzalo Cosa, Dmytro F. Perepichka, Chao-Jun Li
Summary: Recently, the photochemistry of Electron Donor-Acceptor (EDA) complexes using electron donors as catalytic agents has gained interest in the field of catalysis. This methodology allows for the separation of electron transfer from the bond-forming event. In this study, an EDA complex between triarylamines and alpha-perfluorosulfonylpropiophenone reagents was discovered. It catalyzes C-H perfluoroalkylation of arenes and heteroarenes under visible light irradiation in pH- and redox-neutral conditions. The mechanism of this reaction was elucidated through a detailed photophysical characterization of the EDA complex, triarylamine radical cation, and its turnover event.