Article
Chemistry, Multidisciplinary
Fa-Liang Liu, Lan Mei, Ling-Tao Wang, Yu Zhou, Keqi Tang, Ting Li, Rongnan Yi, Wen-Ting Wei
Summary: A novel 5-exo-dig/6-endo-trig bicyclization of 1,6-enynes with sulfonyl hydrazides in the aqueous phase using the cheap and available tetrabutylammonium iodide (TBAI)-tert-butyl hydroperoxide (TBHP) combined system is reported. The resulting reaction of diverse nitrogen- and oxygen-polyheterocycles displays high chemical selectivity, high step-economy, and a moderate substrate scope. Moreover, iodosulfonylation can be realized by modulating the structure of the 1,6-enynes.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Rongxiang Chen, Shaohong Xu, Fumin Shen, Canran Xu, Kaikai Wang, Zhanyong Wang, Lantao Liu
Summary: This method allows for efficient synthesis of sulfonyl chlorides/bromides and their conversion to other functional groups, enabling the synthesis of complex compounds. The reactions are highly selective, simple, and clean, with excellent yields.
Article
Chemistry, Applied
Guofu Zhang, Qiankun Fan, Huimin Wang, Yiyong Zhao, Chengrong Ding
Summary: A new protocol for the synthesis of sulfinic esters via esterification of sulfonyl hydrazides with alcohols using NaHSO3 as the promoter has been developed. This method offers mild transition-metal-free reaction conditions, an inexpensive and readily available reagent, and operational simplicity. Controlled experiments suggest that the transformation likely proceeds through a radical pathway.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Giovanni Centonze, Chiara Portolani, Paolo Righi, Giorgio Bencivenni
Summary: Axially chiral compounds, once viewed as merely a laboratory curiosity, have gained recognition in the past two decades for their significant role in medicinal, biological, and material chemistry. The asymmetric synthesis of atropisomers, particularly N-N atropisomers, has become a rapidly expanding field with new challenges and frontiers. This review highlights recent advances and breakthroughs in the enantioselective synthesis of N-N atropisomers, showcasing the strategies and frameworks involved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Guipeng Feng, Jie Meng, Shaohong Xu, Yao Gao, Yingying Zhu, Ziyu Huang
Summary: A novel Cu-catalyzed radical-radical cross coupling reaction of 3-aminoindazoles with sulfonyl hydrazides has been developed, providing a convenient and efficient synthesis of diverse 1,3-substituted aminoindazoles. This methodology offers readily available starting materials, wide substrate scope, and operational simplicity. Notably, gram-scale reactions have been successfully demonstrated.
Article
Multidisciplinary Sciences
Pouria Patoghi, Ali Sadatnabi, Davood Nematollahi
Summary: In this study, a new convergent paired electro-organic synthesis method for sulfonamide derivatives was introduced, which follows the principles of green chemistry and does not require catalysts, oxidants, halogens, or amines. Instead of using toxic amine compounds, an innovative mechanism based on the reduction of nitro compounds and in-situ production of amine compounds was used. The mechanism involves cathodic reduction of nitro compounds to hydroxylamine compounds and anodic oxidation of hydroxylamine compounds to nitroso compounds.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Multidisciplinary
Mohammad Pirbaba, Rezvan Kardooni, Ali Reza Kiasat, Mohammad Sabaeian
Summary: Solar radiation-assisted green approach was developed for the chemoselective synthesis of 3-alkylated indoles via Yonemitsu-type condensation under catalyst-free conditions. The desired products were formed by one-pot three-component reaction using non-volatile solvent and renewable energy resources. The approach showed good scope and generality, and increased economic and environmental effectiveness.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Cong Chen, Jing Chen, Han Wang, Ze-Feng Xu, Shengguo Duan, Chuan-Ying Li
Summary: A catalyst-free cascade reaction between 3-(2-isocyanoethyl)indoles and 1-sulfonyl-1,2,3-triazoles was developed. This dearomative spirocyclization provided an efficient one-step synthesis of various polycyclic indolines bearing spiro-alpha-carboline in moderate to high yields under thermal reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jiajun Yang, Guodong Li, Ke Yu, Bo Xu, Qianjin Chen
Summary: An electrochemical cascade sulfonylation and lactonization process using arylsulfonyl hydrazines as the reactants and alkenes as substrates was developed for the first time. This method avoids the use of toxic metal catalysts or stoichiometric oxidants and can be carried out under mild conditions. The desired gamma-sulfonylated phthalides with broad substrate tolerance were successfully obtained.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhiyuan Qi, Yifan Liu, Qilong Zhang, Panfeng Zhao, Lingfeng Gao, Xu Sun, Gengxiu Zheng
Summary: A water-promoted synthesis method for constructing 3-sulfone propionic acids from sulfonyl hydrazides and alpha, beta-unsaturated propionic acids with high yields was reported in this study. The green synthesis method was promoted by water without the need for any catalyst, ligand, or organic solvent. The D2O control experiment confirmed that the 2-hydrogen atom of 3-sulfone propionic acid is derived from water. Additionally, the 3-sulfone propionic acid derivatives can be directly purified by crystallization without column chromatography.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shi-Ping Wu, Dong-Kai Wang, Qing-Qing Kang, Guo-Ping Ge, Hongxing Zheng, Meiling Zhu, Ting Li, Jun-Qi Zhang, Wen-Ting Wei
Summary: This novel synthetic protocol utilizes a sulfonyl radical to trigger selective iodosulfonylation and bicyclization of 1,6-dienes, demonstrating high selectivity and efficiency, mild reaction conditions, excellent functional group compatibility, and broad substrate scope. It provides a unique platform for precise radical cyclization.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Xi He, Weili Song, Xuemin Liu, Jiamin Huang, Ruilong Feng, Shaodong Zhou, Jianquan Hong, Xin Ge
Summary: A sustainable and general multicomponent cross-coupling method for the synthesis of 3-chalcogenylindoles from indoles using aryl iodides and elemental sulfur under aqueous micellar conditions is developed. Elemental sulfur serves as an eco-friendly and easy-handling sulfur source, generating thiyl radicals. The synergic effect between Cu catalysts and micelles formed by the sugar-based surfactant GluM stabilizes thiyl radicals, enabling C-S coupling with readily available indoles through single-electron transfer. The aqueous micellar system can be recycled and reused with good yields and can also be extended to the conversion of elemental selenium.
Article
Chemistry, Multidisciplinary
Xue Li, WeiBo Liao, Bin Huang, YuanYuan Zhang, JiangWei Wang
Summary: This study presents an efficient transformation of sulfonyl hydrazides into thiosulfonates using NBS/DABCO without the need for any metal catalyst. The method offers mild reaction conditions, moderate to good yields, and a broad substrate scope. A plausible mechanism for the reaction is proposed involving the decomposition of sulfonyl hydrazides and the formation of S(O-2)-S bonds to produce thiosulfonates.
JOURNAL OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Xiaona Rong, Jingwen Guo, Zheqi Hu, Lehao Huang, Yugui Gu, Yuepiao Cai, Guang Liang, Qinqin Xia
Summary: An efficient iodine-mediated coupling reaction of cyclic amines with sulfonyl hydrazides was reported, providing a new route to the synthesis of vinyl sulfone derivatives. Tentative mechanistic studies suggest that this reaction likely proceeds through a radical process.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Liangxin Fan, Xinxin Zhu, Xingyuan Liu, Fangyu He, Guoyu Yang, Cuilian Xu, Xifa Yang
Summary: This review summarizes recent developments in the synthesis of these tricyclic indoles with palladium-catalyzed domino reactions and their applications in the total synthesis of representative natural products.
Article
Chemistry, Multidisciplinary
Sheng Zhang, Lijun Li, Jingjing Li, Jianxue Shi, Kun Xu, Wenchao Gao, Luyi Zong, Guigen Li, Michael Findlater
Summary: The electrochemical arylation is an effective method for arylating alcohols, providing structurally diverse alcohols under mild conditions with good functional group tolerance and readily available starting materials. Research also suggests that there are two possible pathways involved in the alpha-arylation of benzylic alcohols.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Jingjing Li, Sheng Zhang, Kun Xu
Summary: This review discusses the recent breakthroughs achieved in the electrochemical transformations of alpha-keto acids, showcasing their improved efficiencies and selectivities in electrochemical acylation, cyclization, and reductive amination reactions.
CHINESE CHEMICAL LETTERS
(2021)
Review
Chemistry, Organic
Sheng Zhang, Michael Findlater
Summary: This review focuses on cobalt-catalyzed alkene isomerization, including positional isomerization, geometric isomerization, and cycloisomerization. Three main types of reaction mechanism have been discussed to help the reader better understand and make meaningful comparisons.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Wenchao Gao, Luyi Zong, Weilong Wu, Ming Zhu, Wenmin Liu, Yiyang Zhao, Ting Li, Sheng Zhang
Summary: A new method was developed to construct cyclic phosphinamides with various functional groups under mild conditions via an intramolecular electrochemical C-H phosphinamidation process. This method also provided an alternative route to organic electroluminescent materials and P-N ligands.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sheng Zhang, Wenchao Gao, Jianxue Shi, Jingjing Li, Fengyi Li, Yating Liang, Xuan Zhan, Man-Bo Li
Summary: An umpolung addition of dicyanobenzene to alpha,beta-unsaturated alkenes has been developed using an electroreductive strategy. The electrochemical protocol is compatible with challenging substrates, and good regioselectivities are observed in the reaction. The synthetic utility of this electrochemical approach is demonstrated by direct functionalization of two compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Sheng Zhang, Jianxue Shi, Jingjing Li, Man-Bo Li, Guigen Li, Michael Findlater
Summary: This study presents an electrochemical approach for the direct coupling and deoxygenative coupling of alcohols with fluorenones, providing a new pathway for synthesizing high value products. The method features excellent functional-group tolerance, mild reaction conditions, and good scalability.
Article
Chemistry, Multidisciplinary
Sheng Zhang, Michael Findlater
Summary: Convergent paired electrolysis combines anodic and cathodic reactions to provide an energy-efficient and versatile transformation method. However, the physical separation of the two half-electrode reactions makes coupling of the intermediates challenging. This concept article discusses four strategies used in convergent paired electrolysis from the perspective of reaction mechanism.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Sheng Zhang, Yating Liang, Ke Liu, Xuan Zhan, Weigang Fan, Man-Bo Li, Michael Findlater
Summary: This study presents a strategy using hydrogen evolution reaction (HER) to generate carbanions from weakly acidic sp(3) C-H bonds. This approach allows for selective functionalization of C-H bonds without the use of strong bases or complicated procedures, enabling mild and efficient allylation and allenylation reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Physical
Sheng Zhang, Michael Findlater
Summary: Electrochemically driven hydrogen atom transfer (HAT) catalysis is a versatile and effective tool for the transformation of redox-inactive substrates and the functionalization of C(sp(3))-H/Si-H bonds and alkenes. However, its potential has been largely overlooked due to a lack of understanding of its catalytic mechanism and catalyst selection. In this Review, an overview of HAT catalysis applications, mechanistic pathways, physical properties of HAT mediators, and state-of-the-art examples are provided and discussed.
Article
Chemistry, Organic
Xuan Zhan, Guiqi Gao, Yating Liang, Fengyi Li, Ke Liu, Weigang Fan, Sheng Zhang, Man-Bo Li
Summary: Herein, we report a 'green' aminochlorination method of alkenes using acetonitrile and MgCl2 as nitrogen and chlorine sources, respectively. Benzimidazole was used as a reactivity modulator for chlorine radicals, achieving tunable reactivity, chemoselectivity and stereoselectivity in the four-component reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Yating Liang, Xuan Zhan, Fengyi Li, Hong Bi, Weigang Fan, Sheng Zhang, Man -Bo Li
Summary: This study discovered an array of nitrogen-centered radicals that could be readily generated from benzimidazoles under direct electrolysis. These radicals were used as selective hydrogen atom transfer mediators in electrochemical C(sp3)-H aminations, allowing for unconventional site selectivity and reactivity that were otherwise inaccessible. The catalytic mode enabled by the radicals was also extended to various other reactions.
Article
Chemistry, Organic
Fengyi Li, Yating Liang, Xuan Zhan, Sheng Zhang, Man-Bo Li
Summary: An electrochemical redox-neutral C(sp(3))-H amidation was developed using N-alkoxyamide as an amidating reagent. N-alkoxyamides exhibited higher reactivity compared to direct reactions with primary amides. This novel approach allowed for the synthesis of a wide range of bioactive amides and direct derivatization of pharmaceuticals under oxidant- and transition metal-free conditions. Solar energy could be directly utilized in this electrochemical transformation, providing a clean and practical method for amide synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Sheng Zhang, Jia-Shia Liao, Daniel K. Unruh, Guigen Li, Michael Findlater
Summary: A complementary set of base metal catalysts has been developed for regiodivergent alkene hydrosilylations: iron complexes exhibit high selectivity for Markovnikov hydrosilylations, while cobalt complexes provide excellent anti-Markovnikov selectivity. Both systems are highly efficient and tolerant to a wide range of functional groups.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Jianxue Shi, Jingjing Li, Wenjing Zhao, Mengru Cui, Wanying Ni, Lijun Li, Wenmin Liu, Kun Xu, Sheng Zhang
Summary: An electrochemical intramolecular C-H amination approach was developed to construct benzimidazole-fused phenanthridines. This method is compatible with a variety of functional groups and can achieve high regioselectivities under oxidant- and metal-free conditions. It provides an alternative pathway for accessing organic luminophores.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Polymer Science
M. Mustafa Cetin, Sara Shafiei-Haghighi, Jiazhen Chen, Sheng Zhang, Amanda C. Miller, Daniel K. Unruh, Dominick J. Casadonte, Tracy L. Lohr, Tobin J. Marks, Michael F. Mayer, J. Fraser Stoddart, Michael Findlater
JOURNAL OF POLYMER SCIENCE
(2020)
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.
