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学者姓名：廖赛虎
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Abstract ：
Sulfonyl fluorides have widespread applications in many fields, including organic synthesis, chemical biology, drug discovery and materials science. In particular, in the past decade, a number of aliphatic sulfonyl fluorides have been identified showing various biological activities. These applications and appealing features of sulfonyl fluorides have brought about a significant advancement in developing synthetic methods to access sulfonyl fluorides. In this review, we will discuss the recent developments of radical approaches for the synthesis of aliphatic sulfonyl fluorides.
Keyword ：
Aliphatic sulfonyl fluorides Aliphatic sulfonyl fluorides Radical fluorosulfonylation Radical fluorosulfonylation Radical reactions Radical reactions SuFEx click chemistry SuFEx click chemistry Sulfonyl fluorides Sulfonyl fluorides
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| GB/T 7714 | Lin, Lu , Pei, Guanhua , Cao, Zhong-Yan et al. Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides [J]. | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 27 (23) . |
| MLA | Lin, Lu et al. "Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides" . | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 27 . 23 (2024) . |
| APA | Lin, Lu , Pei, Guanhua , Cao, Zhong-Yan , Liao, Saihu . Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides . | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 27 (23) . |
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The development of visible light-regulated polymerizations for precision synthesis of polymers has drawn considerable attention in the past years. In this study, an ancient dye, indigo, is successfully identified as a new and efficient photoacid catalyst, which can readily promote the ring-opening polymerization of lactones under visible light irradiation in a well-controlled manner, affording the desired polyester products with predictable molecular weights and narrow dispersity. The enhanced acidity of indigos by excitation is crucial to the H-bonding activation of the lactone monomers. Chain extension and block copolymer synthesis are also demonstrated with this method. An ancient dye, indigo, is applied to lactone ring-opening polymerization. The excited state acidity of the indigo photocatalyst is utilized to induce hydrogen bond-mediated bifunctional activation, which efficiently catalyzes the visible light-mediated ring-opening polymerization of lactones. image
Keyword ：
indigo indigo photoacid photoacid photopolymerization photopolymerization ring-opening polymerization ring-opening polymerization visible light visible light
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| GB/T 7714 | Sun, Pan , Li, Zixuan , Zhang, Xun et al. Visible Light-Regulated Ring-Opening Polymerization of Lactones by Employing Indigo as a Photoacid Catalyst [J]. | MACROMOLECULAR RAPID COMMUNICATIONS , 2024 , 45 (11) . |
| MLA | Sun, Pan et al. "Visible Light-Regulated Ring-Opening Polymerization of Lactones by Employing Indigo as a Photoacid Catalyst" . | MACROMOLECULAR RAPID COMMUNICATIONS 45 . 11 (2024) . |
| APA | Sun, Pan , Li, Zixuan , Zhang, Xun , Liao, Yun , Liao, Saihu . Visible Light-Regulated Ring-Opening Polymerization of Lactones by Employing Indigo as a Photoacid Catalyst . | MACROMOLECULAR RAPID COMMUNICATIONS , 2024 , 45 (11) . |
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Indoline-fused polycycles are commonly found as a key structural component in numerous natural products and biologically active compounds. In recent times, the incorporation of sulfonyl fluoride groups has drawn significant attention in research due to their potential to enhance or confer new biological activities to molecules. In this study, we report the development of a modular approach for synthesizing FSO2-functionalized cyclobutane-fused indolines by employing an intermolecular [2+2] cycloaddition reaction between indoles and SuFExable ethenesulfonyl fluoride under triplet energy-transfer catalysis. This method features mild reaction conditions, metal-free photocatalysts, and excellent tolerance to various functional groups. Moreover, we demonstrate the feasibility of further modifying the FSO2-functionalized indoline products via SuFEx click reactions, enabling their conjugation with other molecules. image
Keyword ：
Indolines Indolines Intermolecular [2+2] cycloaddition Intermolecular [2+2] cycloaddition Photocatalysis Photocatalysis SuFEx click reactions SuFEx click reactions Sulfonyl fluorides Sulfonyl fluorides
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| GB/T 7714 | Wei, Rongbiao , Pei, Guanhua , Huang, Yao et al. Accessing SuFExable Cyclobutane-Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles [J]. | ADVANCED SYNTHESIS & CATALYSIS , 2024 , 366 (14) : 3117-3122 . |
| MLA | Wei, Rongbiao et al. "Accessing SuFExable Cyclobutane-Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles" . | ADVANCED SYNTHESIS & CATALYSIS 366 . 14 (2024) : 3117-3122 . |
| APA | Wei, Rongbiao , Pei, Guanhua , Huang, Yao , Liao, Saihu . Accessing SuFExable Cyclobutane-Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles . | ADVANCED SYNTHESIS & CATALYSIS , 2024 , 366 (14) , 3117-3122 . |
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By virtue of noninvasive regulations by light, photocontrolled polymerizations have attracted considerable attention for the precision synthesis of macromolecules. However, a cationic polymerization with simultaneous photocontrol and tacticity-regulation remains elusive so far. Herein, we introduce an asymmetric ion-pairing photoredox catalysis strategy that allows for the development of a stereoselective cationic polymerization with concurrent light regulation for the first time. By employing an ion pair catalyst (PC+/*A(-)) consisting of a photoredox active cation (PC+) and a sterically confined chiral anion (*A-) to deliver the stereochemical control, the cationic polymerization of vinyl ethers can be achieved with photocontrol and high isotactic selectivity (up to 91% m) at a remarkable low catalyst loading (50 ppm).
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| GB/T 7714 | Yang, Zan , Liao, Yun , Zhang, Zhengyi et al. Asymmetric Ion-Pairing Photoredox Catalysis for Stereoselective Cationic Polymerization under Light Control [J]. | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (10) : 6449-6455 . |
| MLA | Yang, Zan et al. "Asymmetric Ion-Pairing Photoredox Catalysis for Stereoselective Cationic Polymerization under Light Control" . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146 . 10 (2024) : 6449-6455 . |
| APA | Yang, Zan , Liao, Yun , Zhang, Zhengyi , Chen, Jianxu , Zhang, Xun , Liao, Saihu . Asymmetric Ion-Pairing Photoredox Catalysis for Stereoselective Cationic Polymerization under Light Control . | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 2024 , 146 (10) , 6449-6455 . |
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In recent years, organophotocatalytic polymerizations have received significant interest as they enable metal-free and highly efficient macromolecular syntheses. Herein, we disclose the development of N-arylacridinium salts as an effective class of photocatalysts that could mediate the cationic reversible addition-fragmentation chain transfer (RAFT) polymerization of vinyl ethers with visible light regulation. Owing to their high stability and matched redox potentials with trithiocarbonate chain transfer agents, N-arylacridinium salts are capable of achieving excellent temporal control over this cationic RAFT polymerization at room temperature under the regulation of blue and green light.
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| GB/T 7714 | Liu, Haonan , Chen, Jianxu , Yang, Zan et al. Light-Controlled Cationic RAFT Polymerization of Vinyl Ethers Using N-Arylacridinium Photocatalysts [J]. | MACROMOLECULES , 2024 , 57 (8) : 3751-3756 . |
| MLA | Liu, Haonan et al. "Light-Controlled Cationic RAFT Polymerization of Vinyl Ethers Using N-Arylacridinium Photocatalysts" . | MACROMOLECULES 57 . 8 (2024) : 3751-3756 . |
| APA | Liu, Haonan , Chen, Jianxu , Yang, Zan , Jiang, Liuyin , Liu, Wenya , Ma, Jun-An et al. Light-Controlled Cationic RAFT Polymerization of Vinyl Ethers Using N-Arylacridinium Photocatalysts . | MACROMOLECULES , 2024 , 57 (8) , 3751-3756 . |
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Recently, the introduction of fluorosulfonyl (-SO2F) groups have attracted considerable research interests, as this moiety could often afford enhanced activities and new functions in the context of chemical biology and drug discovery. Herein, we report the design and synthesis of 1-fluorosulfamoyl-pyridinium (FSAP) salts, which could serve as an effective photoredox-active precursor to fluorosulfamoyl radicals and enable the direct radical C-H fluorosulfonamidation of a variety of (hetero)arenes. This method features mild conditions, visible light, broad substrate scope, good group tolerance, etc., and a metal-free protocol is also viable by using organic photocatalysts. Further, FSAP can also be applied to the radical functionalization of alkenes via 1,2-difunctionalization, radical distal migration, tandem radical-polar crossover reactions, etc. In addition, a formal C-H methylamination of (hetero)arenes by combining this radical C-H fluorosulfonamidation with subsequent hydrolysis as well as product derivatization are also demonstrated. 1-Fluorosulfamoyl-pyridinium (FSAP) was designed and synthesized as a redox-active fluorosulfamoyl radical precursor, which can be applied in radical C-H fluorosulfonamidation of a variety of (hetero)arenes. Further utilization in the radical 1,2-functionalization, radical distal migration, tandem radical-polar crossover reactions of olefins is also demonstrated. image
Keyword ：
N-Centered Radicals N-Centered Radicals Photocatalysis Photocatalysis Radical Reactions Radical Reactions SuFEx SuFEx Sulfamoyl Fluorides Sulfamoyl Fluorides
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| GB/T 7714 | Wang, Peng , Lin, Lu , Huang, Yao et al. Radical Fluorosulfonamidation: A Facile Access to Sulfamoyl Fluorides [J]. | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (34) . |
| MLA | Wang, Peng et al. "Radical Fluorosulfonamidation: A Facile Access to Sulfamoyl Fluorides" . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 63 . 34 (2024) . |
| APA | Wang, Peng , Lin, Lu , Huang, Yao , Zhang, Honghai , Liao, Saihu . Radical Fluorosulfonamidation: A Facile Access to Sulfamoyl Fluorides . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (34) . |
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The orthogonality of different types of living polymerizations allows the synthesis of polymers with diverse compositions and functions. However, two or more catalysts are normally required to promote the integrated polymerizations separately, and few could deliver a photocontrol on both polymerizations. Herein, we demonstrate that BINOL (1,1 '-bi-2-naphthol) with appropriate modification can be evolved into a type of dual-function photocatalyst that can exhibit both photoredox and photoacid catalytic activity at the same time. This dual photofunction could enable BINOLs to catalyze the metal-free atom transfer radical polymerization and ring-opening polymerization with simultaneous light regulation. The utility of this orthogonal method is further demonstrated in the one-pot synthesis of PMMA-b-PVL block copolymers with good control on both molecular weight and low dispersity.
Keyword ：
ATRP ATRP organocatalysis organocatalysis photoacids photoacids photoredox catalysis photoredox catalysis ROP ROP
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| GB/T 7714 | Zhang, Xun , Sun, Pan , Ma, Qiang et al. Unlocking the Photoredox and Photoacid Dual Catalytic Activity of BINOLs for the Development of Organocatalytic Orthogonal Polymerization of ATRP and ROP with Light Regulation [J]. | ACS CATALYSIS , 2024 , 14 (12) : 9452-9459 . |
| MLA | Zhang, Xun et al. "Unlocking the Photoredox and Photoacid Dual Catalytic Activity of BINOLs for the Development of Organocatalytic Orthogonal Polymerization of ATRP and ROP with Light Regulation" . | ACS CATALYSIS 14 . 12 (2024) : 9452-9459 . |
| APA | Zhang, Xun , Sun, Pan , Ma, Qiang , Jiang, Yu , Liao, Saihu . Unlocking the Photoredox and Photoacid Dual Catalytic Activity of BINOLs for the Development of Organocatalytic Orthogonal Polymerization of ATRP and ROP with Light Regulation . | ACS CATALYSIS , 2024 , 14 (12) , 9452-9459 . |
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The tacticity of vinyl polymers is a key factor affecting the properties of materials. Recently, organic Bronsted acids have been demonstrated as effective catalysts for the development of highly stereoselective cationic reversible addition-fragmentation chain transfer (RAFT) polymerizations of vinyl ethers, in which the use of RAFT agents could allow the control the molecular weight and tacticity of polymer products simultaneously. However, the effect of RAFT agents on the tacticity-regulation remains elusive and lacks of investigation. In this study, we synthesized four types of RAFT agents and evaluated their influence in the stereoselective cationic polymerization of isobutyl vinyl ether in the presence of PADI as a Bronsted acid catalyst, which unveils that the Z group of RAFT agents could not only affect the polydispersity of the products, but also exert a profound effect on the stereoselectivity. After extensive screening of the RAFT agents, high stereoregularity (isotacticity, 90% m) was obtained when using dithiocarbonate ester-type RAFT agents with a benzyloxy Z group.
Keyword ：
Bronsted acid catalysis Bronsted acid catalysis Chain transfer agents Chain transfer agents RAFT polymerization RAFT polymerization Stereoselective cationic polymerization Stereoselective cationic polymerization Tacticity Tacticity
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| GB/T 7714 | Zhang, Zheng-Yi , Yang, Zan , Liao, Yun et al. Organic Brønsted Acid-Catalyzed Stereoselective Cationic RAFT Polymerization: The Effect of RAFT Agents [J]. | CHINESE JOURNAL OF POLYMER SCIENCE , 2024 , 42 (6) : 711-717 . |
| MLA | Zhang, Zheng-Yi et al. "Organic Brønsted Acid-Catalyzed Stereoselective Cationic RAFT Polymerization: The Effect of RAFT Agents" . | CHINESE JOURNAL OF POLYMER SCIENCE 42 . 6 (2024) : 711-717 . |
| APA | Zhang, Zheng-Yi , Yang, Zan , Liao, Yun , Liao, Sai-Hu . Organic Brønsted Acid-Catalyzed Stereoselective Cationic RAFT Polymerization: The Effect of RAFT Agents . | CHINESE JOURNAL OF POLYMER SCIENCE , 2024 , 42 (6) , 711-717 . |
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This work aimed to develop organic photocatalysts (PCs) that could mediate organocatalytic atom transfer radical polymerization (O-ATRP) under visible light. Through the core-modification of known chromophoric structures and ring-locking to reach a conjugation extension, annulated N-aryl benzo[kl]acridines were identified as effective visible light-responsive photocatalysts. The corresponding selenium-doped structure showed excellent performance in the O-ATRP of methacrylates, which could afford polymer products with controlled molecular weights and low dispersities under the irradiation of visible light at a 100 ppm catalyst loading.
Keyword ：
ATRP ATRP extended conjugation extended conjugation organocatalysis organocatalysis photocatalysts photocatalysts visible light visible light
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| GB/T 7714 | Shao, Hui , Long, Runzhi , Xu, Hui et al. The Development of Visible-Light Organic Photocatalysts for Atom Transfer Radical Polymerization via Conjugation Extension [J]. | MOLECULES , 2024 , 29 (12) . |
| MLA | Shao, Hui et al. "The Development of Visible-Light Organic Photocatalysts for Atom Transfer Radical Polymerization via Conjugation Extension" . | MOLECULES 29 . 12 (2024) . |
| APA | Shao, Hui , Long, Runzhi , Xu, Hui , Sun, Pan , Wang, Guangrong , Li, Yuanming et al. The Development of Visible-Light Organic Photocatalysts for Atom Transfer Radical Polymerization via Conjugation Extension . | MOLECULES , 2024 , 29 (12) . |
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Organocatalytic atom transfer radical polymerization (O-ATRP) as a metal-free controlled polymerization method represents an appealing approach for polymer synthesis in which the organic photocatalyst is critical to the polymerization efficiency and control. Herein, we introduce sulfur-doped anthanthrene (SDA) as a new and effective organic photoredox catalyst (OPC) for O-ATRP by following the photocatalyst design logic of heteroatom-doping of polycyclic arenes (HDPA). SDA could promote the O-ATRP of methacrylate monomers with good control on both molecular weight and low dispersity at 10-100 ppm catalyst loadings under visible light, even under green light in the absence of external electron donors. Further extension of the SDA catalyst to photoinduced electron/energy transfer addition-fragmentation chain-transfer (PET-RAFT) polymerization under green light is also demonstrated. A new family of photoredox catalysts, sulfur-doped anthanthrenes (SDAs), have been successfully developed for metal-free O-ATRP and PET-RAFT polymerization under visible light and even green light.
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| GB/T 7714 | Shao, Hui , Li, Shaojie , Jiang, Yuqing et al. Sulfur-doped anthanthrenes as effective organic photocatalysts for metal-free ATRP and PET-RAFT polymerization under blue and green light [J]. | POLYMER CHEMISTRY , 2024 , 15 (40) : 4134-4140 . |
| MLA | Shao, Hui et al. "Sulfur-doped anthanthrenes as effective organic photocatalysts for metal-free ATRP and PET-RAFT polymerization under blue and green light" . | POLYMER CHEMISTRY 15 . 40 (2024) : 4134-4140 . |
| APA | Shao, Hui , Li, Shaojie , Jiang, Yuqing , Song, Jinshuai , Zhang, Xun , Chen, Jianxu et al. Sulfur-doped anthanthrenes as effective organic photocatalysts for metal-free ATRP and PET-RAFT polymerization under blue and green light . | POLYMER CHEMISTRY , 2024 , 15 (40) , 4134-4140 . |
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