Article
Chemistry, Multidisciplinary
Fengtian Wu, Yanfei Zhao, Yuepeng Wang, Yueting Xu, Minhao Tang, Zhenpeng Wang, Buxing Han, Zhimin Liu
Summary: This study presents a novel hydrogen-bonding and acid cooperative catalysis strategy for the benzylation of arenes with benzyl alcohols. The catalyst used, [SO3H-PMIm][OTf], demonstrates superior performance compared to other acid catalysts and shows tolerance towards a wide range of benzyl alcohols. The study also reveals the activation mechanism of benzyl alcohol by the IL cation and the activation of the C-H bond in arenes by the IL anion. The reaction proceeds at the interface between the IL-based phase and the arene-based phase, and the IL spontaneously separates after the reaction. This metal-free and environmentally friendly protocol has great potential for industrial applications.
Article
Chemistry, Organic
Fang Lv, Jing Xiao, Junchun Xiang, Fengzhe Guo, Zi-Long Tang, Li-Biao Han
Summary: For the first time, H3PO3 was utilized as both the reducing reagent and the promotor in reductive benzylation reactions with aryl aldehydes. The combination of H3PO3/I-2 enabled various aromatic aldehydes to undergo iodination reactions and Friedel-Crafts type reactions with arenes, easily producing benzyl iodides and diarylmethanes in good yields while also leading to intramolecular cyclization reactions to give corresponding cyclic compounds. This novel strategy offers advantages of easy-handling, low-cost, and metal-free conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Huimiao Zhang, Patrick H. Toy
Summary: A halogen bond donor based on a 2,2'-bipyridine framework has been synthesized and used to catalyze Friedel-Crafts reactions of furans, yielding good reaction yields with moderate catalyst loading at low temperatures. The catalyst design allows for the potential development of an enantioselective version for stereo-selective catalysis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Anton A. Merkushev, Diana A. Eshmemet'eva, Maxim G. Uchuskin
Summary: A FeCl3-catalyzed protocol was developed for the Friedel-Crafts alkylation of 2-substituted furans with 2-nitrobenzhydrols, yielding 2-(2-nitrobenzyl)furans in good to high yields. The obtained product has demonstrated synthetic utility for the synthesis of substituted oxazino[2,3-a]indole.
Article
Chemistry, Physical
Ryoya Tajima, Takaaki Saito, Takayoshi Arai
Summary: The conventional acid-catalyzed aza-Friedel-Crafts reaction of phenols with imines typically shows ortho-selectivity. However, a chiral bis(imidazolidine) pyridine (PyBidine)-Ni(OAc)(2) catalyst can switch the regioselectivity to para-selectivity. This switch is facilitated by the bulky PyBidine-Ni(OAc)(2) catalyst with a Ph2CHCH2 substituent, resulting in highly para-selective aza-Friedel-Crafts reactions (up to 99:1 para/ortho selectivity).
Article
Chemistry, Organic
Junwei Zhang, Hao Wu, Weixin Zhang, Liming Wang, Ying Jin
Summary: A series of cinchona alkaloid silyl ether derivatives have been successfully used as catalysts for the enantioselective Friedel-Crafts reaction between indoles and isatins, yielding 3-hydroxy-2-oxindoles with high yields (78% to 96%) and excellent enantioselectivities (up to 99% ee). This methodology has broadened the catalyst type and substrate scope.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Nicolas Zeidan, Sergiu Bicic, Robert J. Mayer, David Leboeuf, Joseph Moran
Summary: This study demonstrates that HFIP greatly expands the scope of the Bronsted acid-catalyzed hydroarylation of enamides, and acts as a slow-release reservoir for the key cationic intermediate. The reaction is fast and practical, and can prevent the oligomerization of the substrate.
Article
Chemistry, Organic
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok-Kohn, Simon E. Lewis
Summary: This study presents a method for the synthesis of N-alkoxycarbonyl pyrroles by the condensation of readily available O-substituted carbamates with 2,5-dimethoxytetrahydrofuran. It is demonstrated that N-alkoxycarbonyl protection can impart distinct reactivity to pyrrole in comparison with N-sulfonyl protection.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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
Chemistry, Organic
Huan Zhang, Qi Wang, Lu Huang, Ziye Tian, Shunguang Zhang, Youlai Zhang
Summary: An efficient and straightforward synthetic method for generating indanone fused heterocyclic compounds with a unique tetracyclic isoflavone moiety has been developed. These compounds exhibit a broad range of biological activities, with some showing moderate anticancer activities.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Amjad Ali, Raveena Jajoria, Harish K. Harit, Ravi P. Singh
Summary: In this study, the addition of alpha-ketoamide top-quinone methide initiated by dialkylphosphite in the presence of organic base DBU was explored. The coupling of dialkylphosphites to alpha-ketoamides followed[1,2]-phospha-Brook rearrangement, generating alpha-phosphonyloxy enolates that were subsequently seized by p-quinonemethides. This two-step one-pot 1,6-conjugate addition method provides effective access to a series of isatin-incorporated phosphate-bearing 1,6-adducts with high yield and selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Songjin Guo, Jiayi Chen, Mingjun Yi, Liuli Dong, Aijun Lin, Hequan Yao
Summary: A highly efficient synthesis of unsymmetrical 3,3'-diindolylmethanes has been developed by palladium-catalyzed cascade Heck/cyclization reaction, allowing for the formation of one C-N bond, two C-C bonds and two new rings in one-pot. Precursors allenamides and o-ethynylanilines were utilized to generate in situ indole skeletons, and modification of the methylene unit of diindolylmethane was achieved by treatment with oxidant and silyl nucleophiles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Dwaipayan Das, Agniva Das, Saiful Islam, Asish R. R. Das, Adrita Banerjee, Romit Majumder, Debasish Bandyopadhyay
Summary: An efficient and intriguing method using Rh(II) catalysis has been developed for the preparation of fused furan moieties. The technique involves a one-pot C-H activation/concomitant tandem annulation process using an enolic compound and a beta-keto sulfoxonium ylide as reactants. The synthesis only requires Rh-2(TFA)(4) as the catalyst, removing the need for additional metallic or nonmetallic additives. This transformation of naphthoquinone fused furan into highly decorated naphthoquinone fused indolizines shows great promise in synthetic applications.
Article
Chemistry, Organic
Tsukasa Inishi, Goki Hirata, Takashi Nishikata
Summary: Indoles are found to undergo Michael additions efficiently under the catalysis of a cationic iron salt, allowing smooth reactions with beta-mono- and disubstituted enones. The highly active cationic iron catalyst achieves a maximum TON of 425, and enables chemoselective Michael additions of substrates containing both enone and alpha,beta-unsaturated ester moieties.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Nobukazu Taniguchi, Kenji Kitayama
Summary: In this study, the Mo-catalyzed hydroarylation of alkenes at room temperature was explored. The procedure showed good regioselectivity in obtaining a mixture of para- and ortho-isomers with a high yield using electron rich arenes. Furthermore, the reaction of allylic acetates was also investigated, resulting in the formation of allyl arenes through the leaving of acetoxy group.
TETRAHEDRON LETTERS
(2023)
Article
Clinical Neurology
Xicai Sun, Quan Liu, Hongmeng Yu, Huan Wang, Weidong Zhao, Yurong Gu, Houyong Li, Keqing Zhao, Xiaole Song, Dehui Wang, Juan C. Fernandez Miranda, Carl H. Snyderman
Summary: Temporalis muscle flap (TMF) can be effectively used for reconstruction of skull base defects after expanded endoscopic nasopharyngectomy, reducing the occurrence of serious complications in patients with recurrent nasopharyngeal carcinoma.
JOURNAL OF NEUROLOGICAL SURGERY PART B-SKULL BASE
(2022)
Article
Chemistry, Multidisciplinary
Meihao Xia, Yao Chen, Ziran Chen, Wenhao Yu, Haomin Cheng, Chun Feng, Hailiang Ni, Biqin Wang, Keqing Zhao, Ping Hu
Summary: A 1,4-disubstituted 1H-1,2,3-triazoles was successfully synthesized through a catalyst-free click reaction, leading to the formation of a non-covalent palladium chloride complex with unique liquid crystal properties but relatively poor thermal stability. X-ray crystallographic analysis revealed the trans-trans isomeric orientation of the complex, which also showed strip-shaped nanostructures on an oriented graphite substrate.
Article
Chemistry, Applied
Hang Lin, Qiu-Bing Lv, Hai-Feng Wang, Ke-Qing Zhao, Ping Hu, Bi-Qin Wang, Benoit Heinrich, Bertrand Donnio
Summary: Liquid-crystalline D-A dyads and A-D-A triads have been synthesized via Pd-catalyzed Sonogashira coupling/DBU-promoted cyclization reactions, showing spontaneous self-organization into columnar hexagonal or rectangular mesophases over broad temperature ranges. The study reveals that perylenediimide is a stronger electron acceptor compared to benzoperylenediimide, and these donor-acceptor systems have potential applications in various optoelectronic devices.
Article
Chemistry, Multidisciplinary
Yu Du, Cai-Li Zhao, Sheng-Yuan Fan, Wen-Hao Yu, Shi-Kai Xiang, Ke-Qing Zhao, Chun Feng, Bi-Qin Wang
Summary: Seven hydrazide-functionalised triphenylenedicarboxyimides (TDIs) with different polar substitutes connected to the imide N atom were studied to investigate the impact of hydrogen bonding and polar substituents on their mesomorphic properties. It was found that hydrogen bonding was not strong enough to stabilize the columnar mesophase, while dipole-dipole effects favored mesophase stabilities. Additionally, the position of lateral substituents had a significant impact on self-assembly by affecting the overall dipole moment.
Article
Chemistry, Applied
Xue Xia, Cai-Li Zhao, Hong-Tian Xu, Wen-Hao Yu, Shi-Kai Xiang, Lai-Cai Li, Ke-Qing Zhao, Chun Feng, Bi-Qin Wang
Summary: This article describes the synthesis and self-assembly behavior of a series of ten optically active triphenylenedicarboxyimide (TDI) derivatives with a stereogenic center. The TDIs show an enantiotropic hexagonal columnar mesophase with high clearing temperatures. Chiral supramolecular structures are observed in the columnar mesophase of three pairs of chiral TDIs. The axially connected aromatic ring at the stereocenter provides steric repulsion upon stacking, leading to the formation of chiral supramolecular structures. The configuration of the stereogenic center is not the only factor responsible for inducing helical structures in solution.
Article
Chemistry, Multidisciplinary
Dan Xiong, Xiaoping Xiong, Ziran Chen, Wenhao Yu, Chun Feng, Hongmei Chen, Hailiang Ni, Biqin Wang, Keqing Zhao, Ping Hu
Summary: This study investigates the effects of alkyl chain and halogen atom substitution on the mesophase behavior of 1,2,3-triazole-based compounds, aiming to develop novel nematic-phase liquid-crystal materials for optical and photovoltaic devices. The introduction of halogen atoms at the 5-position of 1,2,3-triazole greatly broadens the mesogenic temperature range.
Article
Polymer Science
Jian Chen, Ya Wen, Lingyi Zeng, Xinchun Wang, Hongmei Chen, Wei Min Huang, Yuefeng Bai, Wenhao Yu, Keqing Zhao, Ping Hu
Summary: In this paper, a UV cross-linkable vitrimer-like polymer is synthesized, and it is found that the density of cross-linking and the mechanical properties of the resulting polymers can be tailored via varying the amount of photo-initiator and UV exposure time. The polymers also exhibit good shape memory effect, making them suitable for additive manufacturing applications.
Article
Chemistry, Organic
Ya-Qiong Qi, Shuai Liu, Yan Xu, Yang Li, Tong Su, Hai-Liang Ni, Yuanji Gao, Wenhao Yu, Peng Cao, Ping Hu, Ke-Qing Zhao, Bi-Qin Wang, Bin Chen
Summary: We report an efficient Ni-catalyzed three-component cross-electrophile coupling reaction, which accomplishes dicarbofunctionalization of 1,3-dienes by forming two new C-C bonds in one reaction.
Article
Otorhinolaryngology
Yujie Cao, Xianting Hu, Chun Zhou, Keqing Zhao, Yaoming Zheng, Wenxiu Jiang, Dehui Wang, Huabin Li
Summary: The study found that IL-1 alpha is significantly increased in NP tissues of CRSwNP patients in China and is mainly located in epithelial cells and neutrophils. IL-1 alpha in polyp tissues is associated with the production of IL-8, IL-1 beta, IL-6, IL-4, and IL-13, as well as tissue neutrophil infiltration. In vitro experiments showed that several stimuli, including poly (I:C), lipopolysaccharides, Flagellin, R848, and cytokines (IL-4, IL-5, and IL-13), increase the expression of IL-1 alpha in cultured NECs, and recombinant IL-1 alpha promotes the production of IL-8 and CXCL1.
EUROPEAN ARCHIVES OF OTO-RHINO-LARYNGOLOGY
(2022)
Article
Chemistry, Physical
Min Chen, Tai-Rong Zhang, Wen-Hao Yu, Qiang-Gen Li, Shi-Kai Xiang, Peng Cao, Ke-Qing Zhao, Chun Feng, Bi-Qin Wang
Summary: A series of new mixed tail triphenylene derivatives with specific side chains were synthesized and characterized, and their liquid-crystalline properties and the effects of variations in the lengths of alkoxy and N-alkyl chains on mesogens were studied. It was found that the length of the alkoxy chains had a more significant impact on the mesogens, and the intermolecular hydrogen bonding induced by the amide functional group enhanced the stability of the mesophase. Additionally, it was discovered that intermolecular hydrogen bonding was not the sole factor responsible for gel formation in these molecules.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Engineering, Biomedical
Juan Cen, Runfang Zhang, Tingkui Zhao, Xin Zhang, Chuan Zhang, Jie Cui, Keqing Zhao, Shaofeng Duan, Yuqi Guo
Summary: The article introduces a novel treatment drug for ischemic stroke, SS31-HA-QT, which is a water-soluble compound that can specifically bind to CD44 receptors and be released in the ischemic region. Additionally, the drug can penetrate the blood-brain barrier and target mitochondria. In vitro and in vivo experiments demonstrate that SS31 can enhance drug penetration without toxicity. Furthermore, SS31-HA-QT exerts neuroprotective effects by activating mitophagy.
ADVANCED HEALTHCARE MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Ming-Mei Zhou, Jiao He, Hui-Min Pan, Qing Zeng, Hang Lin, Ke-Qing Zhao, Ping Hu, Bi-Qin Wang, Bertrand Donnio
Summary: This study describes a efficient transition-metal-free arene-fluorine nucleophilic substitution reaction for the straightforward synthesis of several Fluorinated Polycyclic Aromatic Hydrocarbons, and reports the investigation of their liquid crystalline and optical properties.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Dong Yin, Hongyi Shang, Wenhao Yu, Shikai Xiang, Ping Hu, Keqing Zhao, Chun Feng, Biqin Wang
Summary: Introducing different functional groups to the peripheral chains of discotic liquid crystals is a common strategy for designing and synthesizing new promising mesomorphic materials. By modifying the synthesis method, compounds with good thermal stability and high mesophase forming ability were successfully prepared.
ACTA CHIMICA SINICA
(2022)
Article
Materials Science, Multidisciplinary
Hang Lin, Ke-Xiao Zhao, Min Jing, Xiu-Hai Long, Ke-Qing Zhao, Ping Hu, Bi-Qin Wang, Peng Lei, Qing-Dao Zeng, Bertrand Donnio
Summary: This article reports the synthesis of a unique family of liquid-crystalline dimers and their properties. These dimers have multiple functions and can self-assemble into large columnar superlattices. They can also form gels in solvents and exhibit high fluorescence quantum yields. These materials are of great importance in the field of organic electronics.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Chemistry, Multidisciplinary
Wen-Jing Deng, Shuai Liu, Hang Lin, Ke-Xiao Zhao, Xiao-Yan Bai, Ke-Qing Zhao, Ping Hu, Bi-Qin Wang, Hirosato Monobe, Bertrand Donnio
Summary: In this study, two series of regio-isomeric liquid crystalline systems were synthesized and the influence of core topology on their properties was investigated. The beta-isomers showed more extended mesophase ranges, higher phase transition temperatures, and better organic gelling abilities compared to the alpha-isomers. Additionally, the beta-isomers exhibited higher charge carrier mobilities.
NEW JOURNAL OF CHEMISTRY
(2022)
