Article
Chemistry, Multidisciplinary
Hiroki Tashiro, Masahiro Terada, Itaru Nakamura
Summary: Gold-catalyzed reactions were used to synthesize 2H-azirines with sulfenyl and acyl groups at the 3-position, yielding good to excellent results. These reactions involved internal transfer of sulfinyl oxygen atom and carbene insertion into the N-S bond for ring construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Dahye Kang, Justin Kim
Summary: This study describes a bioorthogonal reaction between N,N-dialkylhydroxylamines and cyclooctynes, which features highly regioselective transformation, fast rate, high stability, and excellent chemoselectivity in cell lysate. This reaction introduces a new member to the bioorthogonal reaction compendium outside the prolific class of cycloaddition reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Lei Tang, Yuanjiu Xiao, Feng Wu, Jin-Lan Zhou, Tong-Tong Xu, Jian-Jun Feng
Summary: A silver-catalyzed dearomative cycloaddition strategy is described for the synthesis of indoline fused BCHs. It has high yields, wide functional group tolerance, and provides unexplored chemical space for drug design and development.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Navjeet Kaur, Neha Ahlawat, Yamini Verma, Pooja Grewal, Pranshu Bhardwaj, Nirmala Kumari Jangid
Summary: Metal-mediated formation of heterocycles is an emerging and important strategy in organic chemistry. Silver-assisted cyclic reactions are highly efficient for the synthesis of five-membered fused N-heterocyclic compounds. This review article covers the applications of silver in the preparation of these compounds.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Miguel A. Munoz-Torres, Fernando Martinez-Lara, Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The combination of organolithium chemistry with gold catalysis offers a new synthetic strategy for accessing polysubstituted indoles and carbazoles. This method utilizes ketopyrroles as starting materials and involves a series of reactions to selectively synthesize the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Lin-Jun Qi, Chong-Yang Shi, Peng-Fei Chen, Long Li, Gang Fang, Peng-Cheng Qian, Chao Deng, Jin-Mei Zhou, Long-Wu Ye
Summary: The study presents a novel gold-catalyzed 1,1-carboalkoxylation method for the synthesis of valuable cyclic compounds, enabling asymmetric synthesis through a chirality-transfer strategy. Further mechanistic insight into the distinct migration into gold carbenes is supported by theoretical calculations.
Article
Chemistry, Organic
Xiaoqin Ning, Yongke Chen, Qian Ye, Fangdong Hu, Ying Xia
Summary: A palladium-catalyzed cross-coupling reaction between cyclobutenone N-tosylhadrazones and organohalides has been developed. The reaction involves the generation of a strained allylpalladium intermediate and subsequent electrocyclic ring opening and β-hydride elimination to produce conjugated enynes and enallenes. The broad substrate scope, high yields, and tunable product diversity make this protocol potentially valuable in organic synthesis.
Article
Chemistry, Multidisciplinary
Xiu-Lian Zhang, Jun Gu, Wen-Hao Cui, Zhiwen Ye, Wenbin Yi, Qiang Zhang, Ying He
Summary: This study reports a novel method for the efficient synthesis of configurationally stable axially chiral B,N-heterocycles. By using a stepwise asymmetric synthesis strategy, compounds with two different types of stereogenic axes were successfully constructed. The NH center and pi interactions were found to play an important role in achieving stereoisomerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Motohiro Yasui, Naoko Tahara, Hiroshi Matsubara, Norihiko Takeda, Masafumi Ueda
Summary: This study developed a sequential gold-catalyzed reaction for synthesizing 4-aryl-3-(2H)-isoxazolones with a hydroxy group. The method allows the introduction of an aryl and hydroxy group in a single procedure, exhibiting good chemoselectivity and tolerance towards reactive functional groups.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Jiawei Qiu, Makoto Sako, Tomoyuki Tanaka, Tsuyoshi Matsuzaki, Tsunayoshi Takehara, Takeyuki Suzuki, Shohei Ohno, Kenichi Murai, Mitsuhiro Arisawa
Summary: The developed one-iridium-catalyst system efficiently transforms 1,7-enynes into substituted indole derivatives, providing a straightforward synthetic approach to valuable indoles with vinyl and silylmethyl groups at specific positions.
Article
Chemistry, Multidisciplinary
Qianfeng Qiu, Sirun Yang, Mihael A. Gerkman, Heyifei Fu, Ivan Aprahamian, Grace G. D. Han
Summary: A new type of hydrazone photoswitch was developed, with a macrocyclic structure and phase transition feature, which can store a large amount of energy. It provides a promising strategy for molecular solar thermal energy storage applications.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Bijay Ketan Das, Tanumay Sarkar, Prabhat Kumar Maharana, Subhradeep Kar, Tharmalingam Punniyamurthy
Summary: In this study, stereospecific cascade C-N and C-O bonds formation of oxiranes with N-propargylamines was achieved using Zn/Ag relay catalysis, leading to the synthesis of functionalized dihydrooxazines. The reaction exhibited excellent tolerance towards various functional groups and was scalable for practical applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Fatemeh Arab, Fariba Nazari, Francesc Illas
Summary: Recognition of different structural patterns in different potential energy surface regions is important for understanding the details of physics and chemistry. This study used artificial neural networks to investigate the singlet potential energy surfaces of tetra atomic isomers of the biogenic system [H, C, N, O], and successfully constructed a unified model accurately describing all studied isomers. The developed model has high accuracy and captures the main features of the tetra atomic isomers.
JOURNAL OF CHEMICAL THEORY AND COMPUTATION
(2023)
Article
Chemistry, Applied
Silvia Gonzalez-Pelayo, Olaya Bernardo, Javier Borge, Luis A. Lopez
Summary: The Lewis (or Bronsted) acid-catalyzed reaction of 2-aryl-N-sulfonyl aziridines with ferrocene and ruthenocene leads to the synthesis of new amino-functionalized metallocene derivatives through a regioselective ring opening of the aziridine. These functionalized metallocene derivatives can be used as precursors for the stereoselective synthesis of metallocene analogues of tetrahydroisoquinoline motif by a Pictet-Spengler type reaction. Additionally, isoquinoline analogues can also be accessed through a TfOH-catalyzed three-component reaction involving 2-aryl-N-sulfonyl aziridines, ferrocene (or ruthenocene), and formaldehyde.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Inorganic & Nuclear
Na-Na Li, Ming Yang, Xiao-Jie Xu, Xi-Yan Dong, Si Li, Shuang-Quan Zang
Summary: In this work, organic supramolecular linkers, CB[6] and BPHF@CB[6], were used to assemble dodenuclear silver chalcogenolate clusters into three one-dimensional materials under different synthesis conditions. The crystal structures of these CB[6]-based silver cluster-organic rotaxane frameworks were well resolved, and their emission properties were systematically investigated. This construction strategy involving organic supramolecular linkers provides a new methodology for cluster-assembled materials with intriguing structural and functional properties.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Applied
Linlin Zhu, Qinyong Chen, Ying Wang, Huishan Huang, Wenyi Luo, Zhunxuan Li, Zhen Zhang, Nikos Hadjichristidis
Summary: A facile and effective method involving ring-opening copolymerization of N-sulfonyl aziridines towards cellulose has been developed for efficient oil/water separation. The modified cellulose paper material showed promising properties for efficient oil/water separations, with a grafting ratio ranging from 96 to 150% and a contact angle over 127°.
CARBOHYDRATE POLYMERS
(2021)
Article
Polymer Science
Linlin Zhu, Huishan Huang, Ying Wang, Zhen Zhang, Nikos Hadjichristidis
Summary: A new synthetic methodology for well-defined linear and brush polysulfonamides has been developed through organocatalytic polymerizations. The use of a specific bis(aziridine) monomer suppresses branching from N-sulfonyl aziridines, resulting in controlled linear architectures. The synthesized polysulfonamides exhibit blue fluorescence, excellent thermal properties, and a fast one-pot cascade approach has been developed for brush copolymers with controlled grafted chain length.
Article
Polymer Science
Rui Chen, Ying Wang, Linlin Zhu, Zhen Zhang
Summary: An ultrafast method for controlled synthesis of polysulfonamides through organocatalytic anionic ring-opening polymerization (ROP) in the melt has been established. Using N,N,N',N'',N''-pentamethyldiethylenetriamine (PMDETA) as catalyst, poly(2-methyl-N-tosylaziridine) with molecular weight over 100 kg/mol can be synthesized in less than 90 s. Various initiators can be applied to achieve molecular weight and end-group controlled polymers under open-flask conditions.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Polymer Science
Ying Wang, Linlin Zhu, Wenhao Chen, Zhi Zhou, Zhen Zhang, Nikos Hadjichristidis
Summary: A highly efficient and multicomponent step-growth polymerization via carbene intermediates is established by bimetallic relay catalytic systems. This method overcomes the limitation on the choice of carbene monomers and achieves high-molecular-weight polymers. The results suggest an untapped pathway for the use of metal carbene intermediates to construct new macromolecules.
Article
Polymer Science
Ying Wang, Zhen Zhang
Summary: An efficient synthetic methodology for imidazole-based cross-conjugated polymers has been established through bimetallic Cu(I)/Rh(II) relay-catalyzed multicomponent polymerization. This method utilizes readily available monomers and allows for the synthesis of polymers with tunable optical properties and broad band gaps via one-pot reactions.
Article
Energy & Fuels
Xiangxiang Fu, Xiaohua Deng, Yingjie Deng, Xunhui Xiong, Yuying Zheng, Zhen Zhang, Dai Dang, Gang Wang
Summary: The addition of lithium perchlorate to the electrolyte of lithium metal batteries can prevent dendrite growth and create a uniform and dense solid electrolyte interphase. This study demonstrates the excellent electrochemical performance of lithium metal batteries, including long cycling lifetime, low hysteresis voltage, and improved cycling stability.
Article
Polymer Science
Qingyong Chen, Jingtong Ye, Linlin Zhu, Jiye Luo, Xiuhua Cao, Zhen Zhang
Summary: In this study, an organocatalytic aziridine-based multicomponent polymerization approach was developed for the synthesis of poly(sulfon-amide urethane)s. The method demonstrated excellent yields and linear polymer structure. Additionally, optically active poly(sulfonamide urethane)s were successfully synthesized from chiral aziridine monomers.
EUROPEAN POLYMER JOURNAL
(2022)
Article
Polymer Science
Huishan Huang, Haixiao Wei, Lu Huang, Ting Fan, Xu Li, Zhen Zhang, Tongfei Shi
Summary: We report a new synthetic approach for cyclic polyureas through alternating copolymerization. Aziridines react with tosyl isocyanate spontaneously to produce polyureas with an alternating structure. The synthesized polyureas are found to be cyclic. Calculations indicate that the copolymerization of tosyl isocyanate with ethyleneimine is more favorable kinetically and thermodynamically compared to 2-benzylaziridine.
EUROPEAN POLYMER JOURNAL
(2023)
Article
Polymer Science
Songjie Fan, Peng Zhu, Jingtong Ye, Huishan Huang, Zhen Zhang, Jinxiang Dong
Summary: In this study, an aziridine-based multicomponent polymerization approach was reported to achieve architectural and structural diversity in polymers. Linear and graft poly(sulfonamide ester)s with diverse ester building blocks were efficiently synthesized using aziridine, diol, anhydride, and alcohol. These polymers had thermal stability and can potentially enrich the library of aziridine-based polymeric materials.
Article
Polymer Science
Qingyong Chen, Linlin Zhu, Xu Li, Zhen Zhang
Summary: We introduce a straightforward polymerization methodology for synthesizing poly(sulfonamide thioether)s with optical activity and thermal stability. One of the synthesized polymers, incorporating the diethylene glycol unit, exhibits remarkable mechanical properties and self-healing capabilities.
EUROPEAN POLYMER JOURNAL
(2023)
Article
Energy & Fuels
Xiangxiang Fu, Xiaohua Deng, Yingjie Deng, Xunhui Xiong, Yuying Zheng, Zhen Zhang, Dai Dang, Gang Wang
Summary: Lithium metal is considered to be the most promising electrode for next-generation rechargeable batteries, but poor coulombic efficiency and dendritic lithium growth hinder its practical application. The addition of lithium perchlorate as an additive to the electrolyte forms a uniform and dense solid electrolyte interphase layer, which effectively prevents dendrite growth, improves electrochemical performance, and enhances cycling stability.
Article
Polymer Science
Zhi Zhou, Ying Wang, Linlin Zhu, Dai Dang, Zhen Zhang
Summary: An organocatalytic cycloaddition polymerization approach was developed for the synthesis of thiacyclic polymers. Different bis(N-sulfonyl aziridine)s and diisocyanates were used as monomers, resulting in polymers with diverse photophysical properties.
Article
Polymer Science
Shibin Chen, Linlin Zhu, Zhen Zhang
Summary: This study established a highly efficient catalyst-free synthetic method for optically active polysulfonamide derivatives with controlled linear architecture using chiral bis(2-substituted N-sulfonyl aziridines) as catalysts. Novel poly(sulfonamide amine)s were synthesized through step-growth polymerization, achieving good yields. A one-pot, two-step protocol was developed for the synthesis of poly(sulfonamide dithiocarbamate)s using in situ generated bis(dialkyldithiocarbamate) as the nucleophile. This approach avoided the branches or cross-linkages derived from the homo-polymerization of aziridines.
Article
Polymer Science
Huishan Huang, Wenyi Luo, Linlin Zhu, Ying Wang, Zhen Zhang
Summary: An organocatalytic sequential ring-opening polymerization approach was developed for the synthesis of polysulfonamide-based copolymers, allowing for precise control of molar masses and dispersities. The method involves the use of alcohols and methoxylpolyethylene glycols as initiators, followed by tosyl isocyanate-mediated transformations and ROP reactions. Well-defined triblock and star-shaped copolymers can be successfully prepared from diol and triol initiators.
Article
Polymer Science
Zhunxuan Li, Rui Chen, Ying Wang, Linlin Zhu, Wenyi Luo, Zhen Zhang, Nikos Hadjichristidis
Summary: An efficient synthetic methodology was developed for the modification of hyperbranched polyethyleneimines (PEI) using N-sulfonyl aziridines, resulting in materials with unique fluorescence properties and the ability to remove hazardous metals.
