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学者姓名：廖赛虎
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Abstract ：
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, H. , Long, R. , Xu, H. et al. The Development of Visible-Light Organic Photocatalysts for Atom Transfer Radical Polymerization via Conjugation Extension [J]. | Molecules (Basel, Switzerland) , 2024 , 29 (12) . |
| MLA | Shao, H. et al. "The Development of Visible-Light Organic Photocatalysts for Atom Transfer Radical Polymerization via Conjugation Extension" . | Molecules (Basel, Switzerland) 29 . 12 (2024) . |
| APA | Shao, H. , Long, R. , Xu, H. , Sun, P. , Wang, G. , Li, Y. et al. The Development of Visible-Light Organic Photocatalysts for Atom Transfer Radical Polymerization via Conjugation Extension . | Molecules (Basel, Switzerland) , 2024 , 29 (12) . |
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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. © 2024 Wiley-VCH GmbH.
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, R. , Pei, G. , Huang, Y. et al. Accessing SuFExable Cyclobutane-Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles [J]. | Advanced Synthesis and Catalysis , 2024 , 366 (14) : 3117-3122 . |
| MLA | Wei, R. et al. "Accessing SuFExable Cyclobutane-Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles" . | Advanced Synthesis and Catalysis 366 . 14 (2024) : 3117-3122 . |
| APA | Wei, R. , Pei, G. , Huang, Y. , Liao, S. . Accessing SuFExable Cyclobutane-Fused Indolines via Photocatalytic Intermolecular [2+2] Cycloaddition of Indoles . | Advanced Synthesis and Catalysis , 2024 , 366 (14) , 3117-3122 . |
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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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Abstract ：
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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Motivated by the success of 9,9 '-spirobifluorene (SBF) in optoelectronic materials, we synthesized a novel spiro compound, spirophenanthrene (SP). Incorporating a phenanthrene unit as the core, we aimed to leverage the pi-conjugation of SPs to surpass the limitations of SBF. Experimental and theoretical studies revealed significant advantages over SBF, including red-shifted wavelengths, tunable LUMO energy levels, and enhanced thermal stability. These advantages suggest the potential of SPs as versatile building blocks for diverse optoelectronic devices.
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| GB/T 7714 | Zhang, Yuying , Song, Kanghui , Wang, Tongtong et al. The Synthesis and Properties of Spirophenanthrene [J]. | JOURNAL OF ORGANIC CHEMISTRY , 2024 , 89 (17) : 12044-12048 . |
| MLA | Zhang, Yuying et al. "The Synthesis and Properties of Spirophenanthrene" . | JOURNAL OF ORGANIC CHEMISTRY 89 . 17 (2024) : 12044-12048 . |
| APA | Zhang, Yuying , Song, Kanghui , Wang, Tongtong , Wu, Shuai , Xu, Gang , Liao, Saihu et al. The Synthesis and Properties of Spirophenanthrene . | JOURNAL OF ORGANIC CHEMISTRY , 2024 , 89 (17) , 12044-12048 . |
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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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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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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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