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TsCl-promoted sulfonylation of quinoline N-oxides with sodium sulfinates in water 被引量:6
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作者 Sha Peng Yan-Xi Song +5 位作者 Jun-Yi He Shan-Shan Tang Jia-Xi Tan Zhong Cao Ying-Wu Lin Wei-Min He 《Chinese Chemical Letters》 SCIE CAS CSCD 2019年第12期2287-2290,共4页
An eco-friendly protocol for the synthesis of various 2-sulfonyl quinolines/pyridines through sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal-and oxidant-fre... An eco-friendly protocol for the synthesis of various 2-sulfonyl quinolines/pyridines through sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal-and oxidant-free conditions has been developed.The mild reaction conditions,high reaction efficiency,operational simplicity,short reaction time and remarkable functional-group compatibility make the developed protocol very attractive for the preparation of 2-sulfonyl N-heteroaromatic compounds. 展开更多
关键词 Quinoline N-oxides 2-Sulfonylquinolines Sodium sulfinates sulfonylation In water
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Visible-light-irradiated tandem sulfonylation/cyclization of indole tethered alkenes for the synthesis of tetrahydrocarbazoles 被引量:1
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作者 Yingjie Yu Aiyao Liu +3 位作者 Jingrui He Chengting Wang Haibo Mei Jianlin Han 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第11期4886-4890,共5页
A visible-light-mediated reaction of indole derivatives employing arylsulfonyl chlorides as sulfonyl surrogates has been developed,which proceeds via the sequence of reduction of sulfonyl chloride,sulfonylation,and in... A visible-light-mediated reaction of indole derivatives employing arylsulfonyl chlorides as sulfonyl surrogates has been developed,which proceeds via the sequence of reduction of sulfonyl chloride,sulfonylation,and intramolecular cyclization.This mild protocol transforms a diverse array of indole tethered alkenes and simple sulfonyl chlorides into highly valuable functionalized tetrahydrocarbazoles in good yields.This reaction is also suitable for gram-scale synthesis,which provides an efficient and green access to multi-substituted tetrahydrocarbazoles. 展开更多
关键词 Visible-light-irradiation sulfonylation Tetrahydrocarbazoles INDOLES Tandem radical reaction Sulfonyl chlorides
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Metal-free C(sp^(2))-H perfluoroalkylsulfonylation and configuration inversion:Stereoselective synthesis ofα-perfluoroalkylsulfonyl E-enaminones
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作者 Qing Yu Yunyun Liu Jie-Ping Wan 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第11期3514-3517,共4页
The perfluoroalkylsulfonylation(CF_(3)SO_(2),C_(2)F_(5)SO_(2)and CHF_(2)SO_(2))in the enaminone C-H bonds has been developed simply via the promotion of molecular iodine by using stable and cheap sodium perfluoroalkyl... The perfluoroalkylsulfonylation(CF_(3)SO_(2),C_(2)F_(5)SO_(2)and CHF_(2)SO_(2))in the enaminone C-H bonds has been developed simply via the promotion of molecular iodine by using stable and cheap sodium perfluoroalkyl sulfinates as coupling partners.The stereoselective synthesis of E-configuratedα-perfluoroalkylsulfonyl enaminones has been realized via unprecedented C-H bond elaboration and C=C double bond configuration inversion by free radical process. 展开更多
关键词 C-H Functionalization ENAMINONE Perfluoroalkyl sulfonylation METAL-FREE Configuration inversion
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Photocatalyzed site‐selective C(sp^(3))‒H sulfonylation of toluene derivatives and cycloalkanes with inorganic sulfinates
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作者 Shaonan Zhang Shi Cao +3 位作者 Yu‐Mei Lin Liyuan Sha Cheng Lu Lei Gong 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 2022年第3期564-570,共7页
The development of practical methods for the direct and selective C(sp^(3))‒H functionalization of hydrocarbons is an attractive topic in synthetic chemistry.Although the radical‐mediated hydrogen atom transfer(HAT)p... The development of practical methods for the direct and selective C(sp^(3))‒H functionalization of hydrocarbons is an attractive topic in synthetic chemistry.Although the radical‐mediated hydrogen atom transfer(HAT)process has shown considerable potential in such reactions,it still faces fundamental problems associated with reactivity and selectivity.Herein,we report a convenient and economic approach to site‐selective C(sp^(3))‒H sulfonylation via photo‐induced HAT catalysis.Employing a conjugated polycyclic quinone as a direct HAT photocatalyst,commercially available inorganic sulfinates as the sulfonylation source,copper triflate as an inexpensive oxidant,a variety of toluene derivatives and cycloalkanes were converted into biologically and synthetically interesting sulfone products under mild conditions.The mechanistic studies reveal that the reaction sequence involves direct HAT‐induced radical formation and a subsequent copper‐mediated organometallic process for the C‒S bond formation.This method offers an appealing opportunity to furnish high value‐added products from abundant hydrocarbon starting materials and inexpensive reagents. 展开更多
关键词 Visible light Photocatalysis C(sp^(3))‐H functionalization sulfonylation Radical
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Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions
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作者 Si-Xue Wu Yi-Kun Zhang +1 位作者 Hong-Wei Shi Jie Yan 《Chinese Chemical Letters》 SCIE CAS CSCD 2016年第9期1519-1522,共4页
A new and convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates and benzotriazoles using molecular iodine as catalyst via the S-N bond formation reaction. This cataly... A new and convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates and benzotriazoles using molecular iodine as catalyst via the S-N bond formation reaction. This catalytic radical sulfonylation proceeds efficiently in air at room temperature under neutral conditions, and in short reaction time, to afford the corresponding N-sulfonylbenzotriazoles in good yields, thus extending the catalytic application of molecular iodine in organic synthesis. 展开更多
关键词 sulfonylation Benzotriazole Sodium sulfinate Molecular iodine Catalysis
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Catalyst-and additive-free selective sulfonylation/cyclization of 1,6-enynes with arylazo sulfones leading to sulfonylated γ-butyrolactams
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作者 Qishun Liu Yufen Lv +3 位作者 Ruisheng Liu Xiaohui Zhao Jiawen Wang Wei Wei 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第1期136-139,共4页
A convenient and regioselective sulfonylation/cyclization of 1,6-enynes with arylazo sulfones has been developed to access a series of sulfonylated γ-butyrolactams.The present reaction could be efficiently conducted ... A convenient and regioselective sulfonylation/cyclization of 1,6-enynes with arylazo sulfones has been developed to access a series of sulfonylated γ-butyrolactams.The present reaction could be efficiently conducted under catalyst-and additive-free conditions,in which C-S and C-C bonds were selectively constructed in one-pot procedure. 展开更多
关键词 CATALYST-FREE Arylazo sulfones 1 6-Enynes Sulfonylatedγ-butyrolactams
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Controllable Construction of Vinyl Sulfones and β-Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes
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作者 Xiang Liu Yuan Zhang +2 位作者 Yi Zheng Changfeng Huang Hua Cao 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第12期1367-1372,共6页
Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions.The electrochemical C—H sulfonylation proceeded smoothly to afford(E)-vinyl sulfones ... Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions.The electrochemical C—H sulfonylation proceeded smoothly to afford(E)-vinyl sulfones with good selectivity in an undivided cell without external oxidant.While aerobic trifunctionalization of alkenes occurred in the presence of KI in the air,which providesβ-keto selenosulfones via the formation of C—O,C—S,and C—Se bonds in one-pot.Following control experiments,a plausible mechanism is proposed to rationalize the experimental results. 展开更多
关键词 Synthetic methods ALKENES Difunctionalization Selenylation sulfonylation
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Electrochemical enabled desaturatedβ-C(sp^(3))-H sulfonylation and phosphonylation of cyclic amines
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作者 Tao Liu Jie Lin +6 位作者 Fangjun Xia Zhenhui Xu Xuying Xia Wei Qian Weihui Zhong Dingguo Song Fei Ling 《Green Synthesis and Catalysis》 2024年第4期297-302,共6页
Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp^(3))-H sulfonylation andphosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP_(2)Fe as the... Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp^(3))-H sulfonylation andphosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP_(2)Fe as the redoxmediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfoneand enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Severalmechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products. 展开更多
关键词 ELECTROCATALYSIS Cyclic amine β-Functionalization sulfonylation PHOSPHONYLATION
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Direct C(sp^(3))-H Sulfonylation of Xanthene Derivatives with Sodium Sulfinates by Oxidative Copper Catalysis 被引量:4
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作者 Qinghao Song He Zhao +2 位作者 Yanping Sun Huanfeng Jiang Min Zhang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2022年第3期371-377,共7页
By employing a readily available CuCI/DDQ catalyst system,we herein report a direct C(sp^(3))-H sulfonylation of xanthene derivates with odorless sodium sulfinates.Various 9H-xanthenes,thioxanthenes,and 9,10-dihydroac... By employing a readily available CuCI/DDQ catalyst system,we herein report a direct C(sp^(3))-H sulfonylation of xanthene derivates with odorless sodium sulfinates.Various 9H-xanthenes,thioxanthenes,and 9,10-dihydroacridines are efficiently transformed into the desired benzylic sulfonyl products via a radical/radical cross-coupling process,proceeding with the merits of broad substrate scope,operational simplicity,good functional group compatibility,and mild reaction conditions. 展开更多
关键词 Oxidation C(sp^(3))-H sulfonylation HETEROCYCLES Radical reactions Sodium sulfinates
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Tunable photocatalytic oxysulfonylation and chlorosulfonylation ofα-CF_(3) alkenes with sulfonyl chlorides
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作者 Peng-Ju Xia Fu Liu +1 位作者 Shu-Hui Li Jun-An Xiao 《Organic Chemistry Frontiers》 SCIE EI 2022年第3期709-714,共6页
Tunable photoredox-catalyzed chlorosulfonylation and oxysulfonylation ofα-trifluoromethylstyrenes with sulfonyl chloride were facilely achieved by simply manipulating the photocatalyst and solvent.This strategy makes... Tunable photoredox-catalyzed chlorosulfonylation and oxysulfonylation ofα-trifluoromethylstyrenes with sulfonyl chloride were facilely achieved by simply manipulating the photocatalyst and solvent.This strategy makes full use of the structural features of sulfonyl chloride to afford diverse bifunctional products ofα-trifluoromethylstyrenes in up to 95%yield with excellent functional group tolerance. 展开更多
关键词 SULFONYL STYRENE simply
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Rhodium-catalyzed addition reactions of benzylic C–H bonds to cyclic N-sulfonyl ketimines viaπ-coordination
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作者 Yuntong Li Hang Shi 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第3期287-291,共5页
Mannich-type reactions are a widely used method for the synthesis of amines due to the readily availability of nucleophiles and electrophiles.However,the inclusion of alkylarenes instead of active carbon pronucleophil... Mannich-type reactions are a widely used method for the synthesis of amines due to the readily availability of nucleophiles and electrophiles.However,the inclusion of alkylarenes instead of active carbon pronucleophiles such as aldehydes and ketones in these addition reactions has been a challenge due to the inherent difficulty of benzylic deprotonation.In this study,we present a novel approach for the construction of N-sulfonyl amines via rhodium-catalyzed addition of unbiased benzylic C–H bonds to cyclic N-sulfonyl ketamines throughπ-coordination.This strategy enables the synthesis of a diverse range of N-sulfonyl amines,and subsequent diversification of the addition products showcases the synthetic potential of this protocol. 展开更多
关键词 Benzylic deprotonation Cyclic N–sulfonyl ketimines π-Coordination Mannich-type addition Rhodium catalysis
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Recent advances in the application of sulfinic acids for the construction of sulfur-containing compounds 被引量:1
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作者 Yufen Lv Huanhuan Cui +2 位作者 Na Meng Huilan Yue Wei Wei 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第1期97-114,共18页
Sulfur-containing organic compounds display wide applications in the field of materials science,synthetic chemistry,and pharmaceutical industry.Thus,numerous synthetic strategies have been developed for the synthesis ... Sulfur-containing organic compounds display wide applications in the field of materials science,synthetic chemistry,and pharmaceutical industry.Thus,numerous synthetic strategies have been developed for the synthesis of sulfur-containing compounds in synthetic chemistry.In recent years,the utilization of sulfinic acids as versatile synthons has emerged as attractive and powerful approach to access various organosulfur compounds through sulfonylation,sulfinylation or sulfenylation reactions.In this review,we summarized the recent progress in the construction of various sulfur-containing compounds from sulfininc acids.Selected examples of substrates and the related reaction mechanisms are described here.This review intends to provide readers a comprehensive understanding on the synthesis of sulfur-containing molecules from sulfinic acids and provide help for future synthetic research. 展开更多
关键词 Sulfur-containing compounds Sulfinic acids sulfonylation Sulfinylation SULFENYLATION
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Introduction of N,N’-disulfonylhydrazines as new sulfonylating reagents for highly efficient synthesis of(E)-β-iodovinyl arenesulfones under mild conditions
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作者 Dongping Luo Lin Min +3 位作者 Weiping Zheng Lidong Shan Xinyan Wang Yuefei Hu 《Chinese Chemical Letters》 SCIE CAS CSCD 2020年第7期1877-1880,共4页
N,N’-Disulfonylhydrazines have been proven to be the most reactive precursors of the sulfonyl radicals among all types of sulfonyl substituted hydrazines as early as half a century ago.However,the sulfonyl radicals g... N,N’-Disulfonylhydrazines have been proven to be the most reactive precursors of the sulfonyl radicals among all types of sulfonyl substituted hydrazines as early as half a century ago.However,the sulfonyl radicals generated from these compounds have not been used in organic synthesis except the simple selfdimerization synthesis of disulfones controlled by the"solvent-cage-effects".In this article,N,N’-disulfonylhydrazines were introduced as new sulfonylating reagents and their combinations with NIS were disclosed as new iodosulfonylating reagents of allcynes.Finally,a highly efficient method for the synthesis of(E)-β-iodovinyl arenesulfones was developed by mixing an alkyne,a N,N’-disulfonylhydrazine and NIS in aqueous THF at room temperature for 5 min. 展开更多
关键词 ALKYNES Radical reactions N N’-Disulfonylhydrazines Iodosulfonylation Sulfonyl radicals
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Bis(trifluoromethylsulfonyl)phenylamines as Internal Donors for Ziegler-Natta Polymerization Catalysts 被引量:5
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作者 Li Huashu Yi Jianjun Cui Chunming 《China Petroleum Processing & Petrochemical Technology》 SCIE CAS 2008年第3期51-54,共4页
Several bis(trifluoromethylsulfonyl)phenylamines have been synthesized and used as internal donors for the preparation of heterogeneous Ziegler-Natta catalysts for propylene polymerization. These new cata- lysts are... Several bis(trifluoromethylsulfonyl)phenylamines have been synthesized and used as internal donors for the preparation of heterogeneous Ziegler-Natta catalysts for propylene polymerization. These new cata- lysts are highly active and stereospecific in combination with an external donor for the polymerization of propylene. The activity of these catalysts is dramatically influenced by the electronic capability of the phenyl substituents on the sulfonyl phenylamines. Therefore, the performances of the catalysts can be modified by adjusting the electronic property of the phenyl substituents of the sulfonyl phenylamines. 展开更多
关键词 Ziegler-Natta catalyst PROPYLENE sulfonyl phenylamines internal electron donor POLYPROPYLENE
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Synthesis and characterization of mixing soft-segmented waterborne polyurethane polymer electrolyte with room temperature ionic liquid 被引量:5
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作者 Yue Jiao Li Feng Wu Ren Jie Chen 《Chinese Chemical Letters》 SCIE CAS CSCD 2009年第5期519-522,共4页
Composite polymer electrolytes based on mixing soft-segment waterborne polyurethane (WPU) and 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide (BMImTFSI) have been prepared and characterized. The ... Composite polymer electrolytes based on mixing soft-segment waterborne polyurethane (WPU) and 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide (BMImTFSI) have been prepared and characterized. The addition of BMImTFSI results in an increase of the ionic conductivity. At high BMImTFSI concentration (BMImTFSI/WPU = 3 in weight ratio), the ionic conductivity reaches 4.27 × 10^-3 S/cm at 30 ℃. These composite polymer electrolytes exhibit good thermal and electrochemical stability, which are high enough to be applied in lithium batteries. 展开更多
关键词 Composite polymer electrolytes Ionic liquid Waterborne polyurethane Ionic conductivity 1-Butyl-3-methylimidazoliumbis[(trifluoromethyl) sulfonyl]imide
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H_(4)SiW_(12)O_(40)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3,4-disubstituted 1H-pyrazoles 被引量:1
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作者 Guoping Yang Xuanjie Xie +5 位作者 Mengyuan Cheng Xiaofei Gao Xiaoling Lin Ke Li Yuanyuan Cheng Yufeng Liu 《Chinese Chemical Letters》 SCIE CAS CSCD 2022年第3期1483-1487,共5页
A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H_(4)SiW_(12)O_(40))-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides... A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H_(4)SiW_(12)O_(40))-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides/aldehydes were smoothly reacted with sulfonyl hydrazides to furnish regioselectivity 3,4-disubstituted 1H-pyrazoles. The application of such an earth-abundant, readily accessible, and nontoxic catalyst provides a green approach for the construction of 3,4-disubstituted 1H-pyrazoles. A plausible reaction mechanism has been proposed on the basis of control experiments, GC-MS and DFT calculations. 展开更多
关键词 Silicotungstic acid EPOXIDES ALDEHYDES Sulfonyl hydrazides 3 4-Disubstituted 1H-pyrazoles
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Silver(I)-mediated reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides:Unexpected formation of vinvl sulfones 被引量:1
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作者 Gui Sheng Deng Teng Fei Sun 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第10期1115-1118,共4页
A novel reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides was performed in the presence of silver nitrate or triflate. Conjugated vinyl sulfones as dramatic products were obtained in moderate yield... A novel reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides was performed in the presence of silver nitrate or triflate. Conjugated vinyl sulfones as dramatic products were obtained in moderate yields and with Z-selectivity. A free radical mechanism has been proposed to account for the formation of the products. 展开更多
关键词 Alkynyl trirnethylsilane Sulfonyl chlorides Vinyl sulfones Silver nitrate
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Metal-free visible-light-induced oxidative cyclization reaction of 1,6-enynes and arylsulfinic acids leading to sulfonylated benzofurans 被引量:1
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作者 Leilei Wang Min Zhang +5 位作者 Yulong Zhang Qishun Liu Xiaohui Zhao Jiang-Sheng Li Zidan Luo Wei Wei 《Chinese Chemical Letters》 SCIE CAS CSCD 2020年第1期67-70,共4页
A new and convenient visible-light-induced method has been developed for the synthesis of sulfonylated benzofurans via oxidative cyclization reaction of 1,6-enynes and arylsulfinic acids.This reaction was carried out ... A new and convenient visible-light-induced method has been developed for the synthesis of sulfonylated benzofurans via oxidative cyclization reaction of 1,6-enynes and arylsulfinic acids.This reaction was carried out under metal-free and mild conditions,in which the C-S,C-C and C=O bonds could be sequentially formed in one pot operation. 展开更多
关键词 METAL-FREE Visible-light-catalysis 1 6-Enynes Oxidative cyclization Sulfonylated benzofurans
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Recent progress in the synthesis of sulfonyl fluorides for SuFEx click chemistry 被引量:1
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作者 Tao Zhong Zhida Chen +2 位作者 Jitao Yi Gui Lu Jiang Weng 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第9期2736-2750,共15页
Since the sulfur(Ⅵ)fluoride exchange reaction(SuFEx)was introduced by Sharpless and co-workers in 2014,this new-generation click chemistry has emerged as an efficient and reliable tool for creating modular intermolec... Since the sulfur(Ⅵ)fluoride exchange reaction(SuFEx)was introduced by Sharpless and co-workers in 2014,this new-generation click chemistry has emerged as an efficient and reliable tool for creating modular intermolecular connections.Sulfonyl fluorides,one of the most important sulfur(Ⅵ)fluoride species,have attracted enormous attention in diverse fields,ranging from organic synthesis and material science,to chemical biology and drug discovery.This review aims to introduce seminal and recent progresses on the synthetic methods of sulfonyl fluorides,which include aromatic,aliphatic,alkenyl,and alkynyl sulfonyl fluorides.While not meant to be exhaustive,the purpose is to give a timely overview and insight in this field,and stimulate the development of more efficient synthetic methods of sulfonyl fluorides. 展开更多
关键词 Click chemistry Sulfur(Ⅵ)fluoride exchange Sulfonyl fluorides Fluorine chemistry Synthetic methods
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Synthesis and bioactivities of some new 1H-pyrazole derivatives containing an aryl sulfonate moiety 被引量:2
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作者 Babasaheb V.Kendre Mahadev G.Landge +1 位作者 Wamanrao N.Jadhav Sudhakar R.Bhusare 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第4期325-328,共4页
A new series of 1H-pyrazole derivatives 5a-j bearing an aryl sulfonate moiety have been synthesized by a one-pot cyclo-condensation reaction of 2-(3-(dimethylamino)acryloyl)phenyl-4-methyl benzene sulfonates 4a-e ... A new series of 1H-pyrazole derivatives 5a-j bearing an aryl sulfonate moiety have been synthesized by a one-pot cyclo-condensation reaction of 2-(3-(dimethylamino)acryloyl)phenyl-4-methyl benzene sulfonates 4a-e and hydrazine hydrate or phenyl hydrazine in ethanol under reflux conditions. Some of the newly synthesized compounds were screened for their anti-inflammatory activity. All synthesized compounds were screened against Gram positive and Gram negative bacterial and fungal strains. The compound 5b was found to be a potent anti-inflammatory agent while the majority of the compounds were found to be active against microbial strains. 展开更多
关键词 PyrazoleEnaminonep-Toluene sulfonyl chlorideAnti-inflammatory activityCOX-2 inhibitors
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