Article
Chemistry, Organic
Bubul Das, Anjali Dahiya, Ashish Kumar Sahoo, Bhisma K. Patel
Summary: The isocyanate group in aryl isocyanates acts as a transformable transient directing group, leading to the ortho olefination reaction and the formation of o-alkenylanilines. In alcoholic solvents, aryl isocyanates are converted into carbamates, initiating the insertion of acrylates via ortho C-H activation. Specifically, tAmOH serves as both a solvent and a transient directing mediator. The o-alkenylanilines are further transformed into azacoumarins and C-4 aryl-substituted azacoumarins through Pd(II)-catalyzed C-H functionalizations using aryl iodides as coupling partners.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Lukass Lukasevics, Aleksandrs Cizikovs, Liene Grigorjeva
Summary: An efficient protocol for the C(sp(2))-H carbonylation of amino acid derivatives based on an inexpensive cobalt(II) salt catalyst is reported. The method utilizes picolinamide as a traceless directing group and Co(dpm)(2) as the catalyst, allowing for a broad range of phenylalanine derivatives bearing diverse functional groups to be tolerated. Moreover, the method can be successfully applied for the C(sp(2))-H carbonylation of short peptides, enabling access for peptide late-stage carbonylation.
Article
Chemistry, Inorganic & Nuclear
Sangeeta Kumari, Charu Sharma, Avinash K. Srivastava, Naveen Satrawala, Kamal N. Sharma, Raj K. Joshi
Summary: A Ru(II) complex was synthesized for C-H bond activation alkenylation of arenes using thioether directing groups, achieving high yields under milder conditions compared to previous methods utilizing precious noble metal catalysts. Broad substrate scope was demonstrated with good tolerance towards benzyl thioethers and vinyl, making it the first report of its kind utilizing a Ru-based catalyst for thioether alkenylation.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Huiyeong Seo, Sungwoo Hong
Summary: This study reports a highly enantio- and regioselective Ni-catalyzed hydroamination of unactivated alkenes. It is applicable to common but unreactive alkenes and has a broad range of amine coupling partners, showing great potential for late-stage functionalization of complex molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Hui Xie, Mei Zhong, Xiao-Tong Wang, Jia-Qiang Wu, Yan-Qu Cai, Jidan Liu, Bing Shu, Tong Che, Shang-Shi Zhang
Summary: This study presents a novel method for the direct C(sp(2))-H amination of arenes using Cp*Ir(iii) and Cp*Rh(iii) catalysts with the assistance of a thioether directing group. The protocol is redox-neutral, has a broad substrate scope, high functional-group compatibility, and generates the desired products in moderate to excellent yields. This represents the first example of a thioether-directed Cp*Ir(iii) and Cp*Rh(iii)-catalyzed C(sp(2))-H amination reaction, and also demonstrates the use of azide compounds as a diversified and robust aminating reagent in thioether-directed C-H functionalization reactions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Sebastian Martinez-Flores, Cesar A. Mujica-Martinez, Luis A. Polindara-Garcia
Summary: A Pd(II)-catalyzed C(sp(2)/sp(3))-H bond arylation protocol has been developed for the synthesis of ortho-diaryl, ortho-mono-aryl, and biaryl-diarylmethane-glycinamide derivatives bearing picolinamide as a directing group. Mechanistic details were investigated through computational modeling using DFT calculations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yi-Hao Li, Yuxin Ouyang, Nikita Chekshin, Jin-Quan Yu
Summary: Pd(II)-catalyzed site-selective beta- and gamma-C(sp3)-H arylation of primary aldehydes is achieved by rational design of L,X-type transient directing groups (TDG). External 2-pyridone ligands are crucial for the observed reactivity. By minimizing the loading of acid additives, the ligand effect is enhanced to achieve high reactivities of the challenging primary aldehyde substrates. Site selectivity can be switched by changing the bite angle of TDG to match the desired palladacycle size, as supported by experimental and computational investigations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jiayu Zhou, Dan Liu, Chaolumen Bai, Agula Bao, Tegshi Muschin, Menghe Baiyin, Yong-Sheng Bao
Summary: A novel method for achieving regiodivergent C(sp(3))-H and C(sp(2))-H polyfluoroalkoxylation in the o-methyl benzaldehyde framework by altering the transient directing group is disclosed. The selectivity is proposed to be governed by the size of the palladacycle generated from Pd-chelation with different transient directing groups. This approach provides a new avenue for controlled regiodivergent C(sp(3))-H and C(sp(2))-H functionalization reactions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Karunanidhi Murali, Luana A. Machado, Renato L. Carvalho, Leandro F. Pedrosa, Rishav Mukherjee, Eufranio N. Da Silva Junior, Debabrata Maiti
Summary: C-H functionalization has made significant advancements in synthetic organic chemistry, offering promising prospects in drug development and molecular architecture. The employment of novel metal catalysts and metal-free organic ligands has enabled selective activation of C-H bonds, overcoming previous challenges faced by chemists.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Javed Y. Shaikh, Anindita Bhowmick, Abhijit Chatterjee, Nitin A. Thombare, Ramakrishna G. Bhat
Summary: The palladium (II) catalyzed direct C3-(sp(2))-H alkenylation of five membered heterocyclic aldehydes has been developed using 3-aminobutanoic acid as a catalytic transient directing group. This method allows for highly site-selective C3-alkenylation of heterocyclic aldehydes with various acrylates, featuring exclusive E-selectivity and a broad substrate scope. Additionally, this protocol has proven to be useful in the construction of mechanochromic luminogens.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Multidisciplinary Sciences
Zhipeng Lin, Uttam Dhawa, Xiaoyan Hou, Max Surke, Binbin Yuan, Shu-Wen Li, Yan-Cheng Liou, Magnus J. Johansson, Li-Cheng Xu, Chen-Hang Chao, Xin Hong, Lutz Ackermann
Summary: Electrochemistry, with the aid of data science and artificial intelligence, is increasingly being used for molecular synthesis. The authors have successfully utilized electrocatalyzed C-H activations for selective alkenylation in late-stage drug diversification. This approach eliminates the need for directing groups, which simplifies the synthesis process and reduces waste.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Yi-Hao Li, Yuxin Ouyang, Nikita Chekshin, Jin-Quan Yu
Summary: Pd(II)-catalyzed gamma-C(sp3)-H (hetero)arylation of aliphatic ketones using alpha-amino acids as transient directing groups (TDG) has been developed. By reducing the loading of acid additives, the crucial ligand effect of 2-pyridone is enhanced, leading to improved reactivity and the possibility of cyclic gamma-methylene C(sp3)-H arylation of ketones. Mechanistic investigation and comparison to the gamma-C-H arylation of aldehydes provide structural insights for designing site-selective TDGs.
Article
Chemistry, Multidisciplinary
Jin-Tang Cheng, Li-Jun Xiao, Shao-Qun Qian, Zhe Zhuang, An Liu, Jin-Quan Yu
Summary: In this study, we report the first example of selective Pd(II)-catalyzed tertiary C-H activation of cyclobutylmethyl ketones using a transient directing group. An electron-deficient 2-pyridone ligand was identified as the optimal external ligand to achieve tertiary C-H activation. Various cyclobutylmethyl ketones with quaternary carbon centers were obtained in high yields without the need for preinstalling internal directing groups, and showed high regioselectivity for tertiary C-H arylation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Kausani Ghatak, Han Vinh Huynh
Summary: A library of neutral and cationic palladium complexes of cis-chelating hetero-dicarbene ligands have been prepared and their catalytic activities have been studied. It was found that complexes containing more distinct NHC units exhibited superior catalytic performance.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Hengrui Huo, Yuefa Gong
Summary: Heterocyclic rings are fundamental building blocks in biological systems and have wide applications in synthetic chemistry and medicinal science. The development of novel synthetic methodologies for constructing heterocyclic skeletons from various starting materials has made significant progress in recent decades. Additionally, highly strained cyclopropenes as reactive reagents have attracted much attention in organic transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xing Yang, Liwen Wei, Yuelin Wu, Liejin Zhou, Xinglong Zhang, Yonggui Robin Chi
Summary: In this study, a novel bridged biaryl containing medium-sized rings was selectively synthesized via N-heterocyclic carbene organocatalysis. The reaction began with the addition of the carbene catalyst to the aminophenol-derived aldimine substrate, followed by oxidation and intramolecular desymmetrization to form 1,3-oxazepine-containing bridged biaryls with high yields and excellent enantioselectivities. These products can be readily transformed into chiral phosphite ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Engineering, Environmental
Caiyan Yue, Long Chen, Heng Zhang, Jinshu Huang, Hao Jiang, Hu Li, Song Yang
Summary: Water pollution is a pressing global environmental issue due to the presence of toxic organic pollutants. Photocatalysis, particularly using metal-organic frameworks (MOFs), has shown great promise for organic pollutant removal in wastewater treatment. This review summarizes recent advances in MOF-based photocatalysts, including preparation strategies, modification techniques, and applications for organic pollutant degradation. The working mechanisms, heterojunctions, and key parameters affecting the photocatalytic degradation process are also discussed. The future outlook and challenges of MOF materials for removing organic pollutants from water are emphasized.
ENVIRONMENTAL SCIENCE-WATER RESEARCH & TECHNOLOGY
(2023)
Article
Agriculture, Multidisciplinary
Lihui Shao, Su Zhao, Song Yang, Xiang Zhou, Yan Li, Chengpeng Li, Danping Chen, Zhuirui Li, Guiping Ouyang, Zhenchao Wang
Summary: To discover novel antibacterial agents, two series of quinazolinone derivatives with novel structures were synthesized and their bioactivity against plant bacteria was tested. Compound D32 was identified as a potent antibacterial inhibitor against Xanthomonas oryzae pv. Oryzae (Xoo), with better inhibitory capacity compared to the commercial drugs. Further investigation revealed the mechanism of action of D32, which provides clues for the development of new therapeutic strategies.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Agronomy
Wu-Bin Shao, Yan-Mei Liao, Rong-Shuang Luo, Jin Ji, Wan-Lin Xiao, Xiang Zhou, Li-Wei Liu, Song Yang
Summary: In this study, new phenothiazine derivatives were synthesized and evaluated for their inhibitory activity against tobacco mosaic virus (TMV). Compound A(8) exhibited the highest protective activity against TMV, with an EC50 of 115.67 μg/mL, which was significantly superior to the positive controls ningnanmycin and ribavirin. Biochemical assays demonstrated that compound A(8) could inhibit TMV replication by disrupting its self-assembly and also enhance the defense responses of tobacco plants. This research provides valuable insights for the discovery of new agrochemicals to control plant viral diseases.
PEST MANAGEMENT SCIENCE
(2023)
Article
Agronomy
Jiao-Jiao Zhang, Yu-Mei Feng, Jun-Rong Zhang, Wan-Lin Xiao, Shuai-Shuai Liu, Xiang Zhou, Heng Zhang, Pei-Yi Wang, Li-Wei Liu, Song Yang
Summary: A series of simple triclosan derivatives containing isopropanolamine moiety were designed and assessed for their antibacterial behavior. Some compounds showed excellent bioactivity against three destructive bacteria. Compound C-8 displayed high bioactivities towards Xoo and Xac.
PEST MANAGEMENT SCIENCE
(2023)
Article
Agronomy
Zhenxing Li, Binxin Yang, Yue Ding, Xiang Zhou, Zimian Fang, ShuaiShuai Liu, Jie Yang, Song Yang
Summary: A series of phosphonate derivatives containing a 1,2,3-triazole motif were developed and evaluated for their antiviral activity against tobacco mosaic virus (TMV) helicase. The optimized B-17 showed stronger curative activity against TMV compared to the commercial drug Ribavirin. Additionally, B-17 exhibited potential antiviral activity against other viruses and pathogens.
PEST MANAGEMENT SCIENCE
(2023)
Article
Agronomy
Bin-Xin Yang, Zhen-Xing Li, Shuai-Shuai Liu, Jie Yang, Pei-Yi Wang, Hong-Wu Liu, Xiang Zhou, Li-Wei Liu, Zhi-Bing Wu, Song Yang
Summary: Two series of novel cinnamic acid derivatives were designed and synthesized to explore alternative agrochemicals for controlling plant virus and bacterial diseases. The bioassay results showed that these derivatives exhibited excellent antiviral competence, with compound A(5) demonstrating remarkable protective effects against tobacco mosaic virus. This research provides a foundation for the practical application of cinnamic acid derivatives in pesticide exploration.
PEST MANAGEMENT SCIENCE
(2023)
Article
Agronomy
Zhen-Xing Li, Jin-Hong Hu, Rong-Shuang Luo, Tai-Hong Zhang, Yue Ding, Xiang Zhou, Li-Wei Liu, Zhi-Bing Wu, Song Yang
Summary: This study established an efficient screening platform based on natural alkaloids to discover novel compounds targeting TMV helicase. Rutaecarpine from Evodia rutaecarpa (Juss.) Benth showed excellent TMV helicase inhibitory properties (Kd = 1.1 μm, IC50 = 227.24 μm) and demonstrated strong anti-TMV activity. Molecular docking and dynamic simulations revealed that Rutaecarpine could stably bind to the active pockets of the helicase through hydrogen bonding and hydrophobic interactions with low binding energy (ΔG(bind) = -17.8 kcal/mol).
PEST MANAGEMENT SCIENCE
(2023)
Review
Chemistry, Physical
Wenfeng Zhao, Hu Li, Heng Zhang, Song Yang, Anders Riisager
Summary: Ammonia borane (AB) is a promising material for hydrogen storage and has attracted much attention in reductive organic transformations. This review summarizes the recent progress of AB-mediated transfer hydrogenation reactions of various substrates and discusses the synthesis protocols, reaction parameters, product distribution, and reactivity. The mechanism involving the action mode of AB and structure-activity relationships are also discussed, and the challenges and opportunities for AB-enabled transfer hydrogenation reactions are highlighted.
GREEN ENERGY & ENVIRONMENT
(2023)
Article
Chemistry, Multidisciplinary
Ye Meng, Jinshu Huang, Jie Li, Yumei Jian, Song Yang, Hu Li
Summary: By mimicking the key active species of hemoglobin p450 heme monooxygenase, a Fe-N-4 single atom-doped sulfur-containing carbon nitride photocatalyst was prepared and demonstrated to efficiently convert bio-based alcohols and NH2OH dot HCl to nitriles. The Fe-N-4 sites in the catalyst directly capture photogenerated electrons and molecular oxygen to generate superoxide radicals, while the surrounding S atoms confine photogenerated holes. This strategy of constructing atomic sites enhances the photocatalytic activity and selectivity for biomass valorization.
Article
Chemistry, Multidisciplinary
Feng Xu, Zao Li, Li-Long Zhang, Shengqi Liu, Hu Li, Yuhe Liao, Song Yang
Summary: Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels-Alder (DA) cycloaddition-aromatization strategy has attracted attention. Three challenges exist: improving the equilibrium of DA cycloaddition, controlling the regioselectivity of DA adducts, and increasing the stability of the cycloadduct. In this study, an intramolecular cycloaromatization strategy was developed using a defective Zn-BTC-SA catalyst and an acidic ionic liquid to achieve efficient and selective conversion of bio-furfurals to isoindolinones under liquid phase conditions. The protocol showed high yields and scalability.
Article
Chemistry, Multidisciplinary
Long Chen, Yixuan Liu, Heng Zhang, Yuncong Li, Songdang Zhang, Yulin Hu, Hu Li, Song Yang
Summary: Utilization of renewable biomass resources to produce value-added platform molecules, such as anethole, has attracted significant attention. In this study, a green and effective method for the stereoselective conversion of biomass-derived 4'-methoxyphenylacetone into trans-anethole was developed using a bifunctional acid catalyst. The catalyst exhibited a favorable structure with specific surface area, abundant mesopores, acidic sites, hydrophobicity, and stability. The optimized reaction conditions resulted in a high yield and excellent reusability. This catalytic strategy shows promise for the synthesis of anethole and other high-value molecules.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Inorganic & Nuclear
Li-Long Zhang, Yaqiong Su, Dandan Chen, Hongguo Wu, Feng Xu, Hu Li, Song Yang
Summary: NOx is used as an oxidant for direct selective conversion of methane into methanol, but the interconversion of NOx compounds and the easy formation of O-2 have posed challenges in determining its effectiveness. This study proposes a new cooperative multi-functional mechanism strategy using dual oxidants (NO and N2O) to enhance catalytic performance. Compared with normal mechanisms, this strategy shows stronger CH4 adsorption and thermodynamic favorability. It is expected to inspire further research in DSCMM and other catalytic systems.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Li-Long Zhang, Ji Zheng, Jinxing Gu, Zhuochun Huang, Linguo Lu, Hu Li, Zhongfang Chen, Song Yang
Summary: This study investigated 11 phosphotungstic acid-supported single-atom catalysts (SACs) and found that Os-1/PTA SACs exhibited superior catalytic activity for the purification of methane and hydrogen, with the ease of oxidation following the CO > H-2 > CH4 order. It selectively removed CO in water and MeOH without consuming H-2, due to strong Os-PTA interactions and charge transfer mechanism.
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Review
Polymer Science
Wenfeng Zhao, Qinmei Ge, Hu Li, Nan Jiang, Shangwei Chen, Song Yang, Hang Cong
Summary: Using organic polymers as catalysts for CO2 photoreduction is a highly promising approach to addressing energy and environmental issues, due to their outstanding CO2 adsorption capacity, photochemical performance, and tunable structure.
