Article
Chemistry, Organic
Masayuki Kubo, Naomi Inayama, Eisuke Ota, Junichiro Yamaguchi
Summary: Dance reactions on aromatic rings provide a powerful tool in organic chemistry to move functional groups. By combining with transition-metal-catalyzed coupling reactions, dance reactions of halides and pseudohalides offer a unique platform for the synthesis of diverse substituted aromatic compounds.
Article
Chemistry, Multidisciplinary
Xiang-Ting Min, Ding-Wei Ji, Yu-Qing Guan, Shi-Yu Guo, Yan-Cheng Hu, Boshun Wan, Qing-An Chen
Summary: Transition metal catalyzed decarbonylation offers a unique synthetic strategy for new chemical bond formation. The study developed a visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient conditions, revealing the rhodium complex serves as both the catalytic center and photosensitizer. This visible light promoted catalytic decarbonylation strategy opens up new opportunities for re-evaluating old transformations with ligand dissociation as a rate-determining step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Jin-Hua Bai, Xiu-Juan Qi, Wei Sun, Tian-Yang Yu, Peng-Fei Xu
Summary: This report presents a method for Ni-catalyzed intramolecular decarbonylative coupling, allowing the conversion of areneselenol esters to diaryl selenides. The catalyst, which is inexpensive and readily available, can be used under mild reaction conditions to construct structurally diverse diaryl selenides, including heterocyclic and natural product derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Naish Lalloo, Conor E. Brigham, Melanie S. Sanford
Summary: Transition-metal-catalyzed decarbonylative coupling reactions using carboxylic acid derivatives as electrophiles have the advantages of abundant and inexpensive reactants. This Account highlights the development of base-free decarbonylative coupling reactions catalyzed by group 10 metals and discusses the catalyst design guided by stoichiometric organometallic studies. The article also discusses the challenges and future directions in this field.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Chun-Xiao Li, Qian Ning, Wenxuan Zhao, Hou-Ji Cao, Yi-Ping Wang, Hong Yan, Chang-Sheng Lu, Yong Liang
Summary: This study presents a Rh-catalyzed reaction method for constructing various B-cage-C bonds, utilizing removable imine directing groups for different couplings and observing unexpected rearrangement in pyridyl-directed B(4)-C(sp(3)) formation. The scalable protocol offers advantages such as easy access, use of cheap coupling agents, high efficiency, and a broad substrate scope, showcasing great potential for synthesizing diverse carborane derivatives and drug screening.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xinyi Li, Long Liu, Tianzeng Huang, Zhi Tang, Chunya Li, Wenhui Li, Tao Zhang, Zhaohui Li, Tieqiao Chen
Summary: A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis without the use of excess oxidants, providing a relatively general method for preparing internal alkynes.
Article
Chemistry, Organic
Alexander Bunnell, Naish Lalloo, Conor Brigham, Melanie S. Sanford
Summary: This report describes a Pd-catalyzed decarbonylative coupling reaction for the synthesis of difluorobenzyl-substituted (hetero)arenes using (hetero)aryl boronate esters. The reaction was found to be highly selective and effective for a range of electronically diverse boronate esters and substituted difluorobenzyl glutarimides.
Article
Chemistry, Organic
Alejandro Cervantes-Reyes, Aaron C. Smith, Gary M. Chinigo, David C. Blakemore, Michal Szostak
Summary: This study reports a method for the direct synthesis of nitrogen-containing heteroaromatic biaryls by decarbonylative Pd-catalyzed Suzuki cross-coupling. The practical and modular nature of this method enables the synthesis of diverse heterobiaryl products in excellent yields.
Article
Chemistry, Organic
Liu Xiaojie, Xu Biping, Su Weiping
Summary: This study developed a rhodium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling via in-situ generation strategy of acyl fluorides from carboxylic acids, which showed excellent functional group tolerance and provided a new approach to the synthesis of important aryl compounds.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Editorial Material
Chemistry, Multidisciplinary
Reina Nonami, Yusei Morimoto, Kazuya Kanemoto, Yasunori Yamamoto, Tomohiko Shirai
Summary: This article introduces the research conducted by Tomohiko Shirai and his collaborators at the National Institute of Technology Kochi College, Chuo University, and Hokkaido University. The image illustrates the precedence of asymmetric decarbonylative C-C bond formation by the Ir/S-Me-BIPAM complex over aldehyde decarbonylation.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Reina Nonami, Yusei Morimoto, Kazuya Kanemoto, Yasunori Yamamoto, Tomohiko Shirai
Summary: We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. This asymmetric C-C bond formation is achieved through the decarbonylation of aldehydes catalyzed by chiral iridium complexes and the formation of an aryl-iridium intermediate. The reaction shows broad functional group compatibility and generates no waste apart from carbon monoxide.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Joe Massouh, Antoine Petrelli, Virginie Belliere-Baca, Damien Herault, Herve Clavier
Summary: A rhodium(III)-based catalytic system was used to activate C-H bonds in benzaldehyde derivatives and functionalize them with dioxazolones to produce imides. The study emphasized the importance of the directing group's nature for selectively activating aldehydic C-H bonds. The research showed that this transformation could be applied to various dioxazolones, benzaldehyde derivatives, and an acrolein derivative, highlighting the synthetic utility of the rhodium-catalyzed aldehydic C-H amidation reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Jichao Xiao, John Montgomery
Summary: A simple procedure for the nickel-catalyzed defluorinative alkylation of unactivated aliphatic aldehydes is reported. The protocol exhibits broad substrate scope, mild conditions, and a simple catalytic setup.
Article
Chemistry, Organic
Wenzhi Zhang, Fusheng Bie, Jie Ma, Fengyan Zhou, Michal Szostak, Chengwei Liu
Summary: A base-free palladium-catalyzed decarbonylative borylation of aryl anhydrides has been developed, allowing for the synthesis of versatile arylboronate esters via O-C(O) bond activation and decarbonylation. This method exhibits excellent functional group tolerance and wide substrate scope, using bench stable aryl anhydrides as electrophiles in C-B bond formation, with mechanistic studies and functionalization of late-stage pharmaceutical molecules disclosed.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Emma K. Edelstein, Danica A. Rankic, Caroline C. Dudley, Spencer E. McMinn, Donovon A. Adpressa
Summary: A highly efficient Rh-catalyzed conjugate addition reaction for the synthesis of proline analogues was reported. The method exhibited high yield and high levels of diastereo- and enantioselectivity for the desired products. This approach was used to synthesize a variety of 3-substituted proline derivatives from readily available dehydroproline electrophiles and boronic acid nucleophiles.
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.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
