Review
Chemistry, Multidisciplinary
Tingting Li, Zhichao Jin, Yonggui Robin Chi
Summary: This review discusses N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds, categorizing them into 4 types based on activation modes. The achievements, challenges, and future research directions in NHC-catalyzed arene construction processes are summarized. The outlook is based on the authors' opinions and knowledge on the trends of NHC organocatalysis development.
SCIENCE CHINA-CHEMISTRY
(2022)
Review
Chemistry, Organic
Mohammed Sharique, Uttam K. Tambar
Summary: Aromatic compounds are commonly used in pharmaceuticals and functional materials, leading to a focus on synthetic methods for constructing highly functionalized aromatic frameworks from acyclic precursors. Transition metal catalysis and base-promoted benzannulation reactions are widely utilized for this purpose. Recently, organocatalytic approaches such as N-heterocyclic carbene catalysis have emerged as efficient tools for the formation of complexly substituted aryl rings under mild reaction conditions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jie Lv, Yingling Nong, Kai Chen, Qingyun Wang, Jiamiao Jin, Tingting Li, Zhichao Jin, Yonggui Robin Chi
Summary: A N-heterocyclic carbene (NHC)-catalyzed carbonyl nucleophilic substitution reaction between 1-cyclopropylcarbaldehydes and N-sulfonyl imines is developed for the synthesis of linear fi-aminoenone products. The reaction proceeds under mild conditions and provides the desired fi-aminoenones containing cyclopropyl fragments in moderate to excellent yields. The products exhibit excellent trans-diastereoselectivities and all exist as Z-isomers.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Daniele Ragno, Carmela De Risi, Alessandro Massi, Graziano Di Carmine, Sofia Toldo, Costanza Leonardi, Olga Bortolini
Summary: A novel NHC-promoted synthesis method for biologically active isosorbide imidates was described. The method allows the easy synthesis of different benzothiazole products by using accessible aldimines and oxidative conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Lei Dai, Song Ye
Summary: N-heterocyclic carbene (NHC)-catalyzed reactions involving two-electron and radical pathways have been well-established, with the former more developed than the latter in terms of reaction types and enantioselectivity. In the past decade, several elegant NHC-catalyzed radical reactions have been developed, including oxidation of aldehydes, reductive coupling reactions, and reactions via radical homoenolates.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Tsubasa Inokuma, Kentaro Hashimoto, Tatsuya Fujiwara, Chunzhao Sun, Satoru Kuwano, Ken-ichi Yamada
Summary: The remote electronic effect of a chiral aminoindanol-derived N-heterocyclic carbene catalyst on an asymmetric benzoin reaction was investigated. The catalyst containing remote electron-withdrawing substituents increased the enantioselectivity of the reaction, albeit at the expense of the reaction rate. DFT calculations provided a rationale for the enhanced enantioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Le Dung Pham, Red O. Smith-Sweetser, Briana Krupinsky, Carolyn E. Dewey, Jessica R. Lamb
Summary: This study demonstrates that NHC-CDI adducts can be used as masked precursors for switchable organocatalysis, and the CDI substituents can control the reaction profile without changing the NHC structure. By controlling the electronic variations and perturbations on the CDI, the catalytically active temperature and catalyst release range can be controlled.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Jasper S. Moehler, Lena K. Beiersdoerfer, Brenno Masina, Philipp Wechsler, Helma Wennemers
Summary: N-heterocyclic moieties are commonly found in pharmaceuticals and agrochemicals, but pose a challenge for metalorganic and organocatalytic transformations. This study presents tripeptide catalysts for stereoselective conjugate addition reactions between N-heterocyclic substituted aldehydes and electrophiles, achieving high yields and selectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Applied
Xiaoqun Yang, Yi Zhang, Tingting Li, Zhichao Jin
Summary: This review discusses the activations of carbonyl compounds bearing cyclopropyl, epoxyl, azirine, and aziridinyl groups by N-heterocyclic carbene (NHC) organic catalysts. The reactions are introduced and discussed based on the activation modes involved in these transformations. A brief summary of the achievements and challenges in the NHC-catalyzed activation of cyclopropanes and their analogues is provided, along with our perspectives on the future development in this highly active research field.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Tsubasa Inokuma, Ken-ichi Yamada
Summary: Our recent efforts focused on the development of N-Heterocyclic carbene (NHC)-catalyzed asymmetric reactions. We observed the significant effects of remote substitution at the carbene carbon of NHCs in acylation reactions and a significant enhancement of enantioselectivity by the addition of carboxylate anions. By applying this concept, we achieved excellent enantioselectivities in kinetic resolutions of cyclic and acyclic alcohols. The effects of remote substitution were also observed in intramolecular Stetter reaction and intermolecular benzoin reaction.
Article
Chemistry, Organic
Yuan-Yuan Xu, Lei Dai, Zhong-Hua Gao, Song Ye
Summary: The e-benzylation of gamma-alkenyl-gamma-oxidized enals via dual photoredox and N-heterocyclic carbene catalysis has been developed, providing moderate to good yields of e-benzyl-alpha,fi-gamma,(5-bisunsa-turated esters with exclusive regioselectivities. The reaction is proposed to proceed through the generation of a benzyl radical under photocatalysis, followed by its addition to an NHC-bound trienolate intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Keita Tanaka, Martin-Louis Y. Riu, Brian Valladares, Christopher C. Cummins
Summary: In this study, a new class of Azophosphines and N-heterocyclic iminophosphoranes (NHIPs) were successfully synthesized. The NHIPs exhibited tunability of steric demands and good basicity. The facile and scalable synthesis of NHIPs suggests their potential applications in synthetic chemistry.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Keita Tanaka, Martin-Louis Y. Riu, Brian Valladares, Christopher C. Cummins
Summary: This study presents the preparation and cycloaddition reactions of Azophosphines. The results show that these compounds have good adaptability to phosphorus atom substituents and can generate structures similar to cyclic (alkyl)(amino)carbenes. The NHIPs exhibit strong sigma-donor strengths and basicity, and display unique reactivity in certain reactions. The tunability of steric demands and scalability of these compounds suggest that they may have a wide range of applications in synthetic chemistry.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Laura E. English, Matthew D. Jones, David J. Liptrot
Summary: An N-heterocyclic phosphine (NHP) has been investigated as a catalyst for transesterification reactions of commercial polymer samples, displaying high degradation activity towards poly(lactic acid) with methanol. However, attempts to depolymerise other polymers were unsuccessful, and NHP was found to form a new active catalyst under transesterification conditions.
Review
Chemistry, Multidisciplinary
Yi Zhang, Hui Cai, Xiuhai Gan, Zhichao Jin
Summary: This paper provides a systematic review of N-heterocyclic carbene-catalyzed enantioselective kinetic resolutions, dynamic kinetic resolutions, and desymmetrization reactions. The content is organized based on the activation modes involved in these transformations. Future advances in this highly active research field are also discussed from the authors' perspectives.
SCIENCE CHINA-CHEMISTRY
(2023)
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)
Article
Chemistry, Multidisciplinary
Meng Wu, Jian-Bin Zhang, Yi-Wei Xiong, Yong-Xu Zhao, Meng-Ge Zheng, Xia-Li Huang, Fang Huang, Xing-Xing Wu, Xue Li, Wei-Jiao Fan, Lin Hu, Yuan-Yuan Zeng, Xia-Ju Cheng, Ji-Cheng Yue, Juan-Juan Du, Nan-Nan Chen, Wen-Xiang Wei, Qing-Hua Yao, Xiao-mei Lu, Chao Huang, Jiong Deng, Zhi-Jie Chang, He-Bin Liu, Ting C. Zhao, Y. Eugene Chinn
Summary: By regulating the acetylation of extracellular proteins, eSIRT2 can promote cancer cell metastasis, and the deacetylation mechanism of eSIRT2 in tumor microenvironment has been revealed.
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
Hospitality, Leisure, Sport & Tourism
Xingxing Wu, Logan Schuetz, Milae Lee, Laura L. Payne, Kimberly J. Shinew
Summary: The purpose of this study was to investigate the motivations and meanings of being a NDWB season ticket holder among older women. The findings indicated that being season ticket holders fostered a strong sense of identification with the team and allowed the older women to enhance their social contacts and friendships with other women, fostering a sense of community.
JOURNAL OF LEISURE RESEARCH
(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)
