Chiral sulfones bearing an quaternary stereocenter are privileged structural units that are found in a variety of biologically active products and drug molecules. Herein, we present a photoinduced asymmetric Truce-Smiles rearrangement to access chiral sulfones bearing an all-carbon quaternary center through radical sulfur dioxide insertion. By using the valine methyl ester as the chiral auxiliary, the desired chiral sulfones are afforded in good yields with good to excellent stereoselectivities. This protocol features mild reaction conditions, broad substrate scope and good stereospecificity.
{"title":"Accessing chiral sulfones with an all-carbon quaternary stereocenter via photoinduced asymmetric Truce-Smiles rearrangement and radical sulfur dioxide insertion","authors":"Chenxin Wang, Wei Xiao, Jie Wu","doi":"10.1039/d5qo00383k","DOIUrl":"https://doi.org/10.1039/d5qo00383k","url":null,"abstract":"Chiral sulfones bearing an quaternary stereocenter are privileged structural units that are found in a variety of biologically active products and drug molecules. Herein, we present a photoinduced asymmetric Truce-Smiles rearrangement to access chiral sulfones bearing an all-carbon quaternary center through radical sulfur dioxide insertion. By using the valine methyl ester as the chiral auxiliary, the desired chiral sulfones are afforded in good yields with good to excellent stereoselectivities. This protocol features mild reaction conditions, broad substrate scope and good stereospecificity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143819390","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Vinyl-fluorides appended to heterocycles are a broadly underdeveloped family of functionality with potential application in bioactive compounds. Herein, we disclose a cross-coupling strategy for the regio- and stereo-controlled synthesis of Z-β- fluorovinyl indoles exclusively in the C-2 position, for which there is currently no reported routes to. Z-fluorovinyl iodonium salts, which are formed from alkynes through a Ag-catalysed process, engage in a palladium-catalysed C-2 C-H functionalisation of indoles (and pyrroles) to achieve a broad scope of β-fluorovinyl heterocycles in good to excellent yields. Mechanistic studies and product derivatisations are provided.
{"title":"Palladium-Catalysed Regio- and Stereo-Controlled C-2 β- Fluorovinylation of Indoles","authors":"Atul K. Chaturvedi, Alastair J. J. Lennox","doi":"10.1039/d5qo00521c","DOIUrl":"https://doi.org/10.1039/d5qo00521c","url":null,"abstract":"Vinyl-fluorides appended to heterocycles are a broadly underdeveloped family of functionality with potential application in bioactive compounds. Herein, we disclose a cross-coupling strategy for the regio- and stereo-controlled synthesis of Z-β- fluorovinyl indoles exclusively in the C-2 position, for which there is currently no reported routes to. Z-fluorovinyl iodonium salts, which are formed from alkynes through a Ag-catalysed process, engage in a palladium-catalysed C-2 C-H functionalisation of indoles (and pyrroles) to achieve a broad scope of β-fluorovinyl heterocycles in good to excellent yields. Mechanistic studies and product derivatisations are provided.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143822429","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
5,5-Dicarbon-substituted hydantoins are the key skeletons of numerous drugs, but a general method for the enantioselective de novo synthesis of such scaffolds is elusive. On the other hand, Urech hydantoin synthesis (UHS) represents an efficient approach for hydantoin preparation, but its enantioselective variant remains unknown. Based on desymmetrization and kinetic resolution strategies, we disclose herein the first example of asymmetric catalytic UHS, providing synthetically challenging thiohydantoins with high stereoselectivities. Readily accessible 2-amino malonic esters and racemic amino esters were employed to react with isothiocyanates in the presence of chiral acids, respectively. The resulting products can be facilely functionalized and serves as pivotal scaffolds in various drugs. Experimental studies and DFT calculations suggest that an unexpected dynamic kinetic resolution in the ester ammonolysis step is responsible for the enantiocontrol.
{"title":"Enantioselective Catalytic Urech Hydantoin Synthesis","authors":"Wen-Ya Zheng, Zi-Qi Wang, Xing-Zi Li, Zhuo-Chen Li, Hua Wu, Abudu Rexit Abulikemu, Yu-Ping He","doi":"10.1039/d5qo00378d","DOIUrl":"https://doi.org/10.1039/d5qo00378d","url":null,"abstract":"5,5-Dicarbon-substituted hydantoins are the key skeletons of numerous drugs, but a general method for the enantioselective de novo synthesis of such scaffolds is elusive. On the other hand, Urech hydantoin synthesis (UHS) represents an efficient approach for hydantoin preparation, but its enantioselective variant remains unknown. Based on desymmetrization and kinetic resolution strategies, we disclose herein the first example of asymmetric catalytic UHS, providing synthetically challenging thiohydantoins with high stereoselectivities. Readily accessible 2-amino malonic esters and racemic amino esters were employed to react with isothiocyanates in the presence of chiral acids, respectively. The resulting products can be facilely functionalized and serves as pivotal scaffolds in various drugs. Experimental studies and DFT calculations suggest that an unexpected dynamic kinetic resolution in the ester ammonolysis step is responsible for the enantiocontrol.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813751","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Photobiocatalysis, which integrates the strengths of visible-light-catalysis and enzymatic catalysis, has established itself as a pivotal tool for asymmetric synthesis. Over the past decade, several naturally occurring enzymes have been repurposed to catalyze diverse unnatural transformations that are notoriously difficult to realize using traditional methods. This Emerging Review focuses on the advancements in photobiocatalysis published from 2022 to December 2024 and also highlights earlier seminal reports related to the first demonstration. We organize this review by the coupling modes of visible-light and enzymes, including net-reduction photoenzymatic catalysis (typically) through the illumination of enzymatic electron donor-acceptor complexes, redox neutral photoenzymatic catalysis via direct-visible-light excitation of enzymes, and synergistic dual photo-/enzymatic catalysis. With each section, the discussion is categorized by the type of enzyme, emphasizing the underlying mechanistic aspects, evolutionary trajectories and representative substrate scopes. We anticipate that this review will inspire further developments and application of photobiocatalysis.
{"title":"Recent Advances in Repurposing Natural Enzymes for New-to-Nature Asymmetric Photobiotransformations","authors":"Fulu Liu, Xichao Peng, Jinhai Yu, Xiaoqiang Huang","doi":"10.1039/d5qo00470e","DOIUrl":"https://doi.org/10.1039/d5qo00470e","url":null,"abstract":"Photobiocatalysis, which integrates the strengths of visible-light-catalysis and enzymatic catalysis, has established itself as a pivotal tool for asymmetric synthesis. Over the past decade, several naturally occurring enzymes have been repurposed to catalyze diverse unnatural transformations that are notoriously difficult to realize using traditional methods. This Emerging Review focuses on the advancements in photobiocatalysis published from 2022 to December 2024 and also highlights earlier seminal reports related to the first demonstration. We organize this review by the coupling modes of visible-light and enzymes, including net-reduction photoenzymatic catalysis (typically) through the illumination of enzymatic electron donor-acceptor complexes, redox neutral photoenzymatic catalysis via direct-visible-light excitation of enzymes, and synergistic dual photo-/enzymatic catalysis. With each section, the discussion is categorized by the type of enzyme, emphasizing the underlying mechanistic aspects, evolutionary trajectories and representative substrate scopes. We anticipate that this review will inspire further developments and application of photobiocatalysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813750","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We developed practical reaction conditions and procedure for the direct Suzuki–Miyaura cross-coupling (SMCC) of C(sp2)–B(dan) bonds. Below are important notes to successfully execute the direct SMCC: 1) Dehydrated conditions that exclude as much H2O as possible are required, 2) LiOH is a base of choice, 3) dppf is a ligand of choice when using electron-deficient (hetero)aryl halides [(Het)ArX], 4) P(t-Bu)3 is a ligand of choice when using electron-rich (Het)ArX, 5) COD is a ligand of choice when using (Het)ArX with a protic functional group such as NH2 and OH. Taking heed of these notes enables the direct SMCC of the C(sp2)–B(dan) bond by a wide range of substrates with diverse functional groups, giving the following series of coupling products: Ar–Ar, Ar–HetAr, HetAr–HetAr, alkenyl–Ar, and alkenyl–alkenyl. Sequentially executing distinct types of palladium-catalyzed CCs, such as Buchwald–Hartwig CC + SMCC, Mizoroki–Heck reaction + SMCC, and Sonogashira–Hagihara CC + SMCC, allow to access complex π-conjugated molecules. The B(dan) moiety also exhibits outstanding compatibility with Wittig olefination and Sc(OTf)3-catalyzed acetal-forming reaction, enabling molecular transformations that are otherwise impracticable when using ArB(OH)2. Mechanistic studies suggested the involvement of both path A, wherein a boronate species reacts with an arylpalladium halide, and path B, wherein a boron compound reacts with an arylpalladium hydroxide, at the stage of the transmetalation.
{"title":"Direct Suzuki–Miyaura Cross-Coupling of C(sp2)–B(dan) Bonds Designed in Pursuit of Usability","authors":"Hiroki Andoh, Ryo Nakagawa, Tatsuya Akutagawa, Eiko Katata, Teruhisa Tsuchimoto","doi":"10.1039/d5qo00230c","DOIUrl":"https://doi.org/10.1039/d5qo00230c","url":null,"abstract":"We developed practical reaction conditions and procedure for the direct Suzuki–Miyaura cross-coupling (SMCC) of C(<em>sp</em><small><sup>2</sup></small>)–B(dan) bonds. Below are important notes to successfully execute the direct SMCC: 1) Dehydrated conditions that exclude as much H<small><sub>2</sub></small>O as possible are required, 2) LiOH is a base of choice, 3) dppf is a ligand of choice when using electron-deficient (hetero)aryl halides [(Het)ArX], 4) P(<em>t</em>-Bu)<small><sub>3</sub></small> is a ligand of choice when using electron-rich (Het)ArX, 5) COD is a ligand of choice when using (Het)ArX with a protic functional group such as NH<small><sub>2</sub></small> and OH. Taking heed of these notes enables the direct SMCC of the C(<em>sp</em><small><sup>2</sup></small>)–B(dan) bond by a wide range of substrates with diverse functional groups, giving the following series of coupling products: Ar–Ar, Ar–HetAr, HetAr–HetAr, alkenyl–Ar, and alkenyl–alkenyl. Sequentially executing distinct types of palladium-catalyzed CCs, such as Buchwald–Hartwig CC + SMCC, Mizoroki–Heck reaction + SMCC, and Sonogashira–Hagihara CC + SMCC, allow to access complex π-conjugated molecules. The B(dan) moiety also exhibits outstanding compatibility with Wittig olefination and Sc(OTf)<small><sub>3</sub></small>-catalyzed acetal-forming reaction, enabling molecular transformations that are otherwise impracticable when using ArB(OH)<small><sub>2</sub></small>. Mechanistic studies suggested the involvement of both path A, wherein a boronate species reacts with an arylpalladium halide, and path B, wherein a boron compound reacts with an arylpalladium hydroxide, at the stage of the transmetalation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"52 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813749","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A green and metal-free strategy for the synthesis of diverse structural prolinol derivatives through intramolecular aminoalkoxylation of unfunctionalized olefins in up to 96% isolated yields has been reported. This protocol used easily recyclable NIS as catalysis and accomplished in a mild reaction condition which enabled environmentally friendly alcoholic compounds as reaction solvent and alkoxyl sources. Notably, water is generated as the sole byproduct, emphasizing the green nature of the process. Experimental evidence and DFT calculations support a mechanistic pathway proceeding via aziridinium ion formation rather than through iodonium intermediates; subsequent aziridinium ion ring-opening by alcohol affords the desired products. The NIS catalyst is readily regenerated under an oxygen atmosphere, eliminating the need for transition metals or stoichiometric oxidants. This robust and scalable approach thus represents a valuable advance in the synthesis of prolinol derivatives and highlights the potential of cyclic aziridinium ion intermediates in sustainable nitrogen-heterocycle construction.
{"title":"A Metal-free, Green Strategy for Intramolecular Aminoalkoxylation of Unfunctionalized Olefins via Recyclable NIS Catalysis with Water as the Sole Byproduct","authors":"Hui Sun, Liyuan Zhang, Xin Wu, Bin Cui","doi":"10.1039/d5qo00535c","DOIUrl":"https://doi.org/10.1039/d5qo00535c","url":null,"abstract":"A green and metal-free strategy for the synthesis of diverse structural prolinol derivatives through intramolecular aminoalkoxylation of unfunctionalized olefins in up to 96% isolated yields has been reported. This protocol used easily recyclable NIS as catalysis and accomplished in a mild reaction condition which enabled environmentally friendly alcoholic compounds as reaction solvent and alkoxyl sources. Notably, water is generated as the sole byproduct, emphasizing the green nature of the process. Experimental evidence and DFT calculations support a mechanistic pathway proceeding via aziridinium ion formation rather than through iodonium intermediates; subsequent aziridinium ion ring-opening by alcohol affords the desired products. The NIS catalyst is readily regenerated under an oxygen atmosphere, eliminating the need for transition metals or stoichiometric oxidants. This robust and scalable approach thus represents a valuable advance in the synthesis of prolinol derivatives and highlights the potential of cyclic aziridinium ion intermediates in sustainable nitrogen-heterocycle construction.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"10 1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813748","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The synthesis of 2- and 3-substituted [2.2]paracyclophanyl quinolines using two distinct skeletal editing strategies is described. The first approach relies on indole ring expansion and furnishes 3-aryl quinolines with the paracyclophanyl substituent in the 2-position. In contrast, the second uses a paracyclophane-derived carbene precursor and delivers the complementary 3-[2.2]paracyclophanyl quinolines, highlighting skeletal editing as a powerful tool for advancing the synthetic chemistry of [2.2]paracyclophanes.
{"title":"[2.2]Paracyclophane-substituted Quinolines by Skeletal Editing Strategies","authors":"Tilman Köhler, Olaf Fuhr, Stefan Bräse","doi":"10.1039/d5qo00505a","DOIUrl":"https://doi.org/10.1039/d5qo00505a","url":null,"abstract":"The synthesis of 2- and 3-substituted [2.2]paracyclophanyl quinolines using two distinct skeletal editing strategies is described. The first approach relies on indole ring expansion and furnishes 3-aryl quinolines with the paracyclophanyl substituent in the 2-position. In contrast, the second uses a paracyclophane-derived carbene precursor and delivers the complementary 3-[2.2]paracyclophanyl quinolines, highlighting skeletal editing as a powerful tool for advancing the synthetic chemistry of [2.2]paracyclophanes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"103 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813782","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Free borabenzene is aromatic, but when fused with 3D aromatic carborane, it loses its aromaticity. A new series of ortho-carborane-fused boracycles has been successfully synthesized through selective intramolecular C–H borylation, with claims of forming fused 3D/2D aromatic systems. However, our quantum chemical analysis shows that while the boron cage maintains its aromatic character, the boracycle loses its aromaticity. The limited overlap between the π molecular orbitals of the planar boracycle and the n+1 molecular orbitals of the carborane hinders significant electronic delocalization between the two fused components. Our findings reveal that the peripheral σ-aromaticity of the carborane and the π-aromaticity of the boracycle are orthogonal, making a true 3D/2D aromatic system unattainable. In contrast, when the same boracycle is fused to a 2D aromatic polycyclic aromatic hydrocarbon (PAH), it retains partial aromaticity. Thus, the aromaticity of free boratabenzene is lost when fused with 3D aromatic carborane, i.e., it switches from aromatic to non-aromatic when fused to carborane or weakly aromatic when fused to PAHs.
{"title":"Aromaticity Switch of Borabenzene: From Aromatic when Free or Weakly Aromatic when Fused to 2D PAHs to Non-Aromatic when Fused to 3D Carboranes","authors":"Jordi Poater, Zahra Noori","doi":"10.1039/d5qo00449g","DOIUrl":"https://doi.org/10.1039/d5qo00449g","url":null,"abstract":"Free borabenzene is aromatic, but when fused with 3D aromatic carborane, it loses its aromaticity. A new series of ortho-carborane-fused boracycles has been successfully synthesized through selective intramolecular C–H borylation, with claims of forming fused 3D/2D aromatic systems. However, our quantum chemical analysis shows that while the boron cage maintains its aromatic character, the boracycle loses its aromaticity. The limited overlap between the π molecular orbitals of the planar boracycle and the n+1 molecular orbitals of the carborane hinders significant electronic delocalization between the two fused components. Our findings reveal that the peripheral σ-aromaticity of the carborane and the π-aromaticity of the boracycle are orthogonal, making a true 3D/2D aromatic system unattainable. In contrast, when the same boracycle is fused to a 2D aromatic polycyclic aromatic hydrocarbon (PAH), it retains partial aromaticity. Thus, the aromaticity of free boratabenzene is lost when fused with 3D aromatic carborane, i.e., it switches from aromatic to non-aromatic when fused to carborane or weakly aromatic when fused to PAHs.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"108 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813781","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This study presents a transition-metal-free one-pot synthetic strategy for the efficient construction of C3,6-dithioquinolin-2-ones, which employs N-substituted tetrahydroquinolines and disulfides in a direct reaction, utilizing 2-iodoxybenzoic acid (IBX) as the oxidant and water as co-solvent to achieve regioselective oxidative desulfurization and functionalization of quinoline C–H bonds under mild conditions. In contrast to conventional approaches, this protocol eliminates the need for transition-metal catalysts (e.g., Pd, Ru) and directing groups, significantly reducing environmental risks associated with toxic reagents and lowering synthesis costs, and demonstrates high atom and step economy. Furthermore, the mixed solvent system (DCE/H₂O) reduces organic solvent consumption, while the broad substrate scope. Derivatization experiments confirm the straightforward conversion of products into functional molecules, offering a sustainable pathway for synthesizing complex heterocycles and providing a powerful means to expand diverse synthetic routes.
{"title":"Hypervalent Iodine-mediated One-pot Synthesis of C3,6-Dithioquinolin-2-ones","authors":"Yukun Xie, Xiaodan Meng, Chenrui Liu, Xiaoxiang Zhang, Zhuan Zhang, Taoyuan Liang","doi":"10.1039/d5qo00337g","DOIUrl":"https://doi.org/10.1039/d5qo00337g","url":null,"abstract":"This study presents a transition-metal-free one-pot synthetic strategy for the efficient construction of C3,6-dithioquinolin-2-ones, which employs N-substituted tetrahydroquinolines and disulfides in a direct reaction, utilizing 2-iodoxybenzoic acid (IBX) as the oxidant and water as co-solvent to achieve regioselective oxidative desulfurization and functionalization of quinoline C–H bonds under mild conditions. In contrast to conventional approaches, this protocol eliminates the need for transition-metal catalysts (e.g., Pd, Ru) and directing groups, significantly reducing environmental risks associated with toxic reagents and lowering synthesis costs, and demonstrates high atom and step economy. Furthermore, the mixed solvent system (DCE/H₂O) reduces organic solvent consumption, while the broad substrate scope. Derivatization experiments confirm the straightforward conversion of products into functional molecules, offering a sustainable pathway for synthesizing complex heterocycles and providing a powerful means to expand diverse synthetic routes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813777","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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