Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Applied
Daniel Gavina, Marcos Escolano, Javier Torres, Gloria Alzuet-Pina, Maria Sanchez-Rosello, Carlos del Pozo
Summary: Substituted and annulated pyrroles containing chiral centers can be accessed through organocatalytic enantioselective Friedel-Crafts alkylation (FCA) reaction. These compounds are interesting due to their natural occurrence and diverse biological activities. In the past two decades, significant synthetic efforts have been made to develop asymmetric transformations involving pyrroles in the FCA reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Jin Jiaping, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: Here, we report an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles. This protocol provides a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectivities (up to 93% ee) under mild conditions. The utilization of a chiral spirocyclic phosphoric acid is crucial in converting the initial 1H-pyrrol-3-yl carbinols into reactive 3-methide-3H-pyrroles and achieving the desired enantioselective transformation.
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Infectious Diseases
Anne Ardaillou, Jerome Alsarraf, Jean Legault, Francois Simard, Andre Pichette
Summary: This study synthesized a series of derivatives related to natural flavonoids through catalytic Friedel-Crafts alkylation, and evaluated the antibacterial and cytotoxic potential of these novel analogs. The research highlighted the relationship between the structure and pharmacological properties of alkylated dihydrochalcones.
Article
Chemistry, Inorganic & Nuclear
Zubi Sadiq, Ambreen Ghani, Shahida Shujaat, Erum Akbar Hussain, Siham A. Alissa, Munawar Iqbal
Summary: In this study, structurally diverse improvements were made to bis(indolyl)methanes using a multicomponent approach, where SiO2-KHSO4 catalyst was used. The reaction time was significantly reduced and high yields were achieved for the synthesized compounds.
INORGANIC CHEMISTRY COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Bei Zhou, Zhuang Ma, Asma M. Alenad, Carsten Kreyenschulte, Stephan Bartling, Matthias Beller, Rajenahally Jagadeesh
Summary: A general method for cobalt-catalysed CH-alkylation of indoles with alcohols is reported, which allows the easy synthesis of substituted and functionalized indoles in good yields. The resulting products are an interesting class of heterocyclic compounds widely used in organic synthesis and medicinal chemistry.
Review
Chemistry, Organic
Guillermo Caballero-Garcia, Jonathan M. Goodman
Summary: N-Triflylphosphoramides (NTPA) have emerged as popular catalysts for enantioselective transformations due to their stronger Bronsted acid properties compared to phosphoric acids (PA). This review categorizes NTPA-catalyzed reactions based on the enantio-determining step and highlights their use in total synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Physical
Hua-Qi Wang, Shu-Bin Mou, Wen Xiao, Huan Zhou, Xu-Dong Hou, Su-Jing Wang, Qian Wang, Jiali Gao, Zhiyi Wei, Lijun Liu, Zheng Xiang
Summary: CylK is a key enzyme that catalyzes the formation of the cylindrocyclophane scaffold through Friedel-Crafts alkylation reactions, exhibiting regioselectivity and stereospecificity. This study proposes a concerted double-activation mechanism to explain the enzymatic alkylation with regioselectivity and stereospecificity, based on crystal structures, free energy simulations, and site-directed mutagenesis experiments.
Article
Chemistry, Organic
Pan Tang, You -Yuan Wei, Long Wen, Hao-Jie Ma, Yi Yang, Yan Jiang
Summary: This article investigates the MgI2-catalyzed nucleophilic ring-opening reactions of donor-acceptor cyclopropanes with indoline-2-thiones as sulfur nucleophiles. Under mild reaction conditions, a series of functionalized gamma-indolylthio butyric acid derivatives are obtained in good to excellent yields. Additionally, the thioether functionalized ring-opening products can be transformed into sulfone and methionine analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Wenming Chen, Guifang Chen, Biao Wang, Wei Wang, Wei Huang, Xu Tian
Summary: An efficient Bronsted acid-catalyzed Friedel-Crafts-type alkylation method has been developed, which provides access to highly functionalized diarylmethane derivatives in moderate to high yields. Additionally, the product of selected diaryl acetate can be transformed into beta, beta-diaryl substituted gamma-butyrolactone.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Pinglu Zhang, Nobuya Tsuji, Jie Ouyang, Benjamin List
Summary: A novel catalytic asymmetric intramolecular hydroarylation using strong and confined IDPi Bronsted acid catalysts has been demonstrated, enabling efficient and highly enantioselective formation of quaternary stereogenic centers from aliphatic and aromatic olefins with indoles. This transformation has a broad substrate scope and can be further elaborated into bioactive molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Haipeng Hu, Xin Wu, Yuqian Qiu, Cuilin Wang, Wei Wang, Guizhou Yue, Hanguang Wang, Juhua Feng, Guangtu Wang, Hailiang Ni, Ping Zou
Summary: In this study, the dehydrative mono-/dialkylation reactions of alcohols and beta-ketoacids were achieved under arylboronic acid catalysis, leading to the formation of beta-aryl ketones and beta-ketoesters in moderate to high yields. The reaction temperature was found to control the selectivity between decarboxylative alkylation and decarboxylation processes. A possible catalytic cycle was proposed based on experimental evidence.
Article
Chemistry, Multidisciplinary
Qian-Yi Wang, Teng-Fei Liu, Li-Feng Chu, Yun Yao, Chong-Dao Lu
Summary: In the presence of a chiral spiro phosphoric acid catalyst, the asymmetric reaction of disubstituted ketenes with N-H pyrroles occurred to afford enantioenriched C-acylated pyrroles bearing alpha-stereogenic carbon centres. This reaction represents a rare example of catalytic asymmetric reaction of ketenes with carbon-based nucleophiles, with significant research implications.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zhinian Li, Shenliang Wang, Wei Hong, Shihui Zou, Liping Xiao, Jie Fan
Article
Chemistry, Physical
Linfang Lu, Baohui Lou, Shihui Zou, Hisayoshi Kobayashi, Juanjuan Liu, Liping Xiao, Jie Fan
Article
Chemistry, Multidisciplinary
Navpreet K. Sethi, Hisayoshi Kobayashi, Biling Wu, Renhong Li, Jie Fan
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2018)
Article
Chemistry, Physical
Linfang Lu, Zhiqiang Wang, Shihui Zou, Yuheng Zhou, Wei Hong, Renhong Li, Liping Xiao, Juanjuan Liu, Xue-Qing Gong, Jie Fan
JOURNAL OF MATERIALS CHEMISTRY A
(2018)
Article
Chemistry, Physical
Wei Hong, Zhi-Qiang Wang, Shihui Zou, Yuheng Zhou, Linfang Lu, Qiuyue Zhou, Xue-Qing Gong, Jie Fan
Article
Chemistry, Physical
Sha Li, Hui Zhou, Liping Xiao, Jie Fan, Xiaoming Zheng
Article
Engineering, Biomedical
Xiaoqiang Shang, Yun Long Li, Hao Chen, Lisha Yu, Zhugang Wang, Liping Xiao, Jie Fan
JOURNAL OF BIOMATERIALS APPLICATIONS
(2019)
Article
Chemistry, Physical
Sha Li, Chuanhong Jin, Ningdong Feng, Feng Deng, Liping Xiao, Jie Fan
CATALYSIS COMMUNICATIONS
(2019)
Article
Chemistry, Inorganic & Nuclear
Juanjuan Liu, Shihui Zou, Baohui Lou, Changlei Chen, Liping Xiao, Jie Fan
INORGANIC CHEMISTRY
(2019)
Article
Multidisciplinary Sciences
Lisha Yu, Xiaoqiang Shang, Hao Chen, Liping Xiao, Yihan Zhu, Jie Fan
NATURE COMMUNICATIONS
(2019)
Article
Chemistry, Applied
Kaimin Du, Mengjia Hao, Zhinian Li, Wei Hong, Juanjuan Liu, Liping Xiao, Shihui Zou, Hisayoshi Kobayashi, Jie Fan
CHINESE JOURNAL OF CATALYSIS
(2019)
Article
Chemistry, Physical
Qiuyue Zhou, Chongyuan Zhou, Yuheng Zhou, Wei Hong, Shihui Zou, Xue-Qing Gong, Juanjuan Liu, Liping Xiao, Jie Fan
CATALYSIS SCIENCE & TECHNOLOGY
(2019)
Article
Chemistry, Inorganic & Nuclear
Zhou Hui, Li Sha, Xiao Li-Ping, Fan Jie, Zheng Xiao-Ming
CHINESE JOURNAL OF INORGANIC CHEMISTRY
(2018)
Meeting Abstract
Chemistry, Multidisciplinary
Linfang Lu, Shihui Zou, Jie Fan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Applied
Juanjuan Liu, Shihui Zou, Jiachao Wu, Hisayoshi Kobayashi, Hongting Zhao, Jie Fan
CHINESE JOURNAL OF CATALYSIS
(2018)
Article
Chemistry, Physical
Zi-Ye Liu, Qian-Yu Wang, Ji-Ming Hu
Summary: In this study, a layered carbon dot composite catalyst (NiFe LDH@CDs) was prepared using a one-step coprecipitation method, without the need for heating or hydrothermal treatment. The CD-functionalized catalyst facilitated rapid charge transfer and accelerated the oxygen evolution reaction. Additionally, the heterojunction structure formed between NiFe LDH and CDs efficiently suppressed photoelectron-hole recombination.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Rohit Kumar, Ankit Kumar Srivastava, Palaniyappan Nagarasu, Vedichi Madhu, Ekambaram Balaraman
Summary: We designed and synthesized a NN-CoII bidentate complex and used it for the amination of alcohols under mild and solventless conditions. The complex exhibited good reactivity towards both primary and sterically hindered secondary alcohols, providing high yields of amines. The pyrazole moiety in the ligand played a crucial role in the reaction. Furthermore, we demonstrated the reusability of the complex as a homogeneous cobalt catalyst.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Shivanand Chettri, Liang-Ting Wu, Sagarmani Rasaily, Debesh Sharma, Bikram Gurung, Rajani Dewan, Sudarsan Tamang, Jyh-Chiang Jiang, Anand Pariyar
Summary: Replicating the enzymatic surface microenvironment in vitro is challenging, but constructing an analogous model could facilitate our understanding of surface effects and aid in developing an efficient bioinspired catalytic system. In this study, five unique Cu2O morphologies were generated, and the surface morphology variations were found to be a consequence of differences in the exposure of low-index facets. The reactivity of Cu2O was found to be influenced by the proportion of {110} planes, with r-Cu2O exhibiting the highest reactivity.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Yong Tang, Jianhao Qiu, Dingliang Dai, Guanglu Xia, Lu Zhang, Jianfeng Yao
Summary: Defect engineering has been shown to improve the photocatalytic performance. This study investigated the use of defect-rich UiO-66-NH2 wrapped by ZnIn2S4 as a catalyst for photocatalytic H2O2 production. The defects in UiO-66-NH2 enhanced O-2 adsorption and charge separation, leading to higher H2O2 yield. The insights from this work can advance the research in defect engineering of MOFs and photocatalytic H2O2 synthesis.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Ruiyang Qu, Shuxin Mao, Jana Weiss, Vita A. Kondratenko, Evgenii V. Kondratenko, Stephan Bartling, Haifeng Qi, Annette-Enrica Surkus, Kathrin Junge, Matthias Beller
Summary: The hydrogenation of amides, a challenging reaction usually performed at high temperatures, has been achieved under milder conditions using a new Pt-MoOx/TiO2 catalyst. This catalyst system enables the selective hydrogenation of various amides and imides.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Xiaoran Niu, Ao Wang, Lei Tong, Lei Wang, Yuan Kong, Chenliang Su, Hai-Wei Liang
Summary: This study introduces a novel intermetallic PdCu3 catalyst supported on defective nanodiamond-graphene (ND@G), which exhibits high selectivity (95%) and remarkable activity (turnover frequency: 2940 h(-1)), six times higher than that of the commercial Lindlar catalyst.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Review
Chemistry, Physical
Zhiyuan Zheng, Yiming Yue, Hongying Zhuo, Qinggang Liu, Yanqiang Huang
Summary: This review presents the recent research advances on single-atom catalysis for deep reduction of CO2. Detailed introductions and summaries were classified into three categories based on proton-coupled multi-electron transfer approaches: strengthening metal-support interaction, rational design and regulation of coordination environment, and development of SACs with multi-atom active sites. The challenges and future research directions in the field of SACs for CO2 reduction are also proposed.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Shiv Kumar, Paramita Datta, Anup Bhunia, Swadhin K. Mandal
Summary: This article reports a transition-metal-free process for in situ denitrogenation of tosylhydrazones, resulting in the production of various sulfones. The authors used a phenalenyl-based odd alternant hydrocarbon as a photoredox catalyst, which acted as a potent oxidant to facilitate the denitrogenation reaction. The method showed wide functional-group tolerance and high yields, making it suitable for late-stage modification of natural products.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
L. A. Luque-Alvarez, J. Gonzalez-Arias, F. Romero-Sarria, T. R. Reina, L. F. Bobadilla, J. A. Odriozola
Summary: Currently, the production of acetic acid through the carbonylation reaction of methanol has limitations, leading to the exploration of alternative methods using heterogeneous catalysts. This study investigates the methanol carbonylation reaction over a Cu-H-MOR catalyst and proposes a reaction mechanism based on the catalytic behavior and performance of the catalyst. The results provide insights into the reaction mechanism and the involvement of acid and redox centers.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
