Pub Date : 2024-12-24DOI: 10.1021/acs.orglett.4c04257
Wei Li, Lingtong Zhao, Chenchen Diao, Guohai Zhang, Huaifeng Li
A visible light-driven, intermolecular interrupted Barton reaction has been developed for radical-relay sulfonyloximation of alkenes with alkyl nitrites, using DABSO as a trapping reagent. This method overcomes the challenges of competing normal Barton reactions and polarity mismatches by rapidly and irreversibly capturing alkyl radicals, preventing unwanted side reactions. The resulting polarity-reversed sulfonyl radicals undergo highly selective addition to alkenes, yielding α-alkylsulfonyl ketoximes tethered to hydroxyl or ketone groups. Conducted under mild visible light conditions, this approach eliminates the need for harsh mercury lamps, offering a scalable, chemoselective method for synthesizing valuable sulfonylated oxime derivatives.
{"title":"Visible Light-Driven Interrupted Barton Reaction: Intermolecular Radical-Relay Sulfonyloximation of Alkenes with DABSO and Alkyl Nitrites","authors":"Wei Li, Lingtong Zhao, Chenchen Diao, Guohai Zhang, Huaifeng Li","doi":"10.1021/acs.orglett.4c04257","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04257","url":null,"abstract":"A visible light-driven, intermolecular interrupted Barton reaction has been developed for radical-relay sulfonyloximation of alkenes with alkyl nitrites, using DABSO as a trapping reagent. This method overcomes the challenges of competing normal Barton reactions and polarity mismatches by rapidly and irreversibly capturing alkyl radicals, preventing unwanted side reactions. The resulting polarity-reversed sulfonyl radicals undergo highly selective addition to alkenes, yielding α-alkylsulfonyl ketoximes tethered to hydroxyl or ketone groups. Conducted under mild visible light conditions, this approach eliminates the need for harsh mercury lamps, offering a scalable, chemoselective method for synthesizing valuable sulfonylated oxime derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"15 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880227","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}
Pub Date : 2024-12-24DOI: 10.1021/acs.orglett.4c04258
Luke E. Hodson, Paul Joseph Tholath, Leon Jacobs, Nicole Pribut, Gouthami Pashikanti, Aletta E. van der Westhuyzen, David Laws, III, Dennis C. Liotta
The synthetic utility of tetrabenzyl pyrophosphate for achieving chemoselective phosphorylation of phenols, as well as primary, secondary, and tertiary alcohols, is reported here. Additionally, we introduce a rapid, mild, and chemoselective debenzylation procedure, enabling access to phosphates in the presence of redox sensitive groups. Finally, stoichiometrically controlled monodebenzylation provides a versatile platform for late-stage divergent synthesis of phosphodiester and phosphoramidate chemical libraries.
{"title":"Mild and Chemoselective Triethylsilane-Mediated Debenzylation for Phosphate Synthesis","authors":"Luke E. Hodson, Paul Joseph Tholath, Leon Jacobs, Nicole Pribut, Gouthami Pashikanti, Aletta E. van der Westhuyzen, David Laws, III, Dennis C. Liotta","doi":"10.1021/acs.orglett.4c04258","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04258","url":null,"abstract":"The synthetic utility of tetrabenzyl pyrophosphate for achieving chemoselective phosphorylation of phenols, as well as primary, secondary, and tertiary alcohols, is reported here. Additionally, we introduce a rapid, mild, and chemoselective debenzylation procedure, enabling access to phosphates in the presence of redox sensitive groups. Finally, stoichiometrically controlled monodebenzylation provides a versatile platform for late-stage divergent synthesis of phosphodiester and phosphoramidate chemical libraries.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"52 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880228","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}
Pub Date : 2024-12-24DOI: 10.1021/acs.orglett.4c04389
Li Song, Meifang Yang, Mengyu Li, Yanli Qiu, Yili Dai, Jingyu Tian, Xing Zheng, Yitian Zhao, Xu Yao, Houchao Tao
We developed glycosyl N-(para-methoxyphenylpropargyl) pyrrole-2-carboxylates (PPPCs) as highly effective donors for chemical glycosylation. The modular design and exceptional stability of the acid precursor provide PPPC donors with synthetic versatility and ease of use. Activated by NIS/TMSOTf, PPPC donors exhibit a broad compatibility for both O- and N-glycosylation reactions. Their distinct reactivity gradient enables streamlined one-pot syntheses, complementing thioglycosides and imidates. These features position PPPC donors as promising tools for advancing carbohydrate chemistry.
{"title":"N-(para-Methoxyphenylpropargyl) Pyrrole-2-carboxylate (PPPC) Glycosides as Donors for Glycosylation","authors":"Li Song, Meifang Yang, Mengyu Li, Yanli Qiu, Yili Dai, Jingyu Tian, Xing Zheng, Yitian Zhao, Xu Yao, Houchao Tao","doi":"10.1021/acs.orglett.4c04389","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04389","url":null,"abstract":"We developed glycosyl <i>N</i>-(<i>para</i>-methoxyphenylpropargyl) pyrrole-2-carboxylates (PPPCs) as highly effective donors for chemical glycosylation. The modular design and exceptional stability of the acid precursor provide PPPC donors with synthetic versatility and ease of use. Activated by NIS/TMSOTf, PPPC donors exhibit a broad compatibility for both <i>O</i>- and <i>N</i>-glycosylation reactions. Their distinct reactivity gradient enables streamlined one-pot syntheses, complementing thioglycosides and imidates. These features position PPPC donors as promising tools for advancing carbohydrate chemistry.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"149 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142884465","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}
Pub Date : 2024-12-24DOI: 10.1021/acs.orglett.4c04055
Chenhao Yao, Zhaocheng Xu, Jun Tian, Ze Lin, Changqing Zhang, Yunpeng Ge, Lei Zhang, Siyuan Wang, Zeyuan Dong
To explore alkali-cation selectivity at the chemical reaction level, in this work, we for the first time focused on the different behaviors of potassium and sodium ions in intra- and intermolecular arylation. We prepared a series of aromatic foldamers based on pyridine/oxadiazole alternating sequences as the catalysts for the arylation. Our studies revealed that foldamers can selectively recognize K+ over Na+ and the interactions between foldamers and K+ drive the arylation with a significant yield. In contrast, no trace of the product can be found with Na+. Furthermore, foldamers, with biased handedness, can afford products with optical activity. The balance between two enantiomers of products can be freely controlled by the different conformations of foldamers.
{"title":"Alkali-Cation-Selective Arylation Promoted by Ion Recognition of Foldamers","authors":"Chenhao Yao, Zhaocheng Xu, Jun Tian, Ze Lin, Changqing Zhang, Yunpeng Ge, Lei Zhang, Siyuan Wang, Zeyuan Dong","doi":"10.1021/acs.orglett.4c04055","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04055","url":null,"abstract":"To explore alkali-cation selectivity at the chemical reaction level, in this work, we for the first time focused on the different behaviors of potassium and sodium ions in intra- and intermolecular arylation. We prepared a series of aromatic foldamers based on pyridine/oxadiazole alternating sequences as the catalysts for the arylation. Our studies revealed that foldamers can selectively recognize K<sup>+</sup> over Na<sup>+</sup> and the interactions between foldamers and K<sup>+</sup> drive the arylation with a significant yield. In contrast, no trace of the product can be found with Na<sup>+</sup>. Furthermore, foldamers, with biased handedness, can afford products with optical activity. The balance between two enantiomers of products can be freely controlled by the different conformations of foldamers.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"3 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880225","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}
Herein, we present the enantioselective synthesis of 2,3-dihydro-4-quinolones bearing chiral tetrasubstituted carbons from isatins and 2′-aminoacetophenones. The transformation is mediated by a chiral phosphoric acid catalyst and proceeds via an in situ generated ketimine and subsequent enantioselective intramolecular cyclization. The methodology features a broad scope and functional group tolerance with yields and enantioselectivities of up to 99% and 98% ee. Detailed density functional theory (DFT) calculations support the proposed reaction mechanism and the origin of asymmetric induction.
{"title":"Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of 2,2-Disubstituted 2,3-Dihydro-4-quinolones from Isatins and 2′-Aminoacetophenones","authors":"Hidenori Andatsu, Yuto Terashima, Rio Kawamura, Yoichiro Matsuda, Tsunayoshi Takehara, Takeyuki Suzuki, Naoki Yasukawa, Shuichi Nakamura","doi":"10.1021/acs.orglett.4c04249","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04249","url":null,"abstract":"Herein, we present the enantioselective synthesis of 2,3-dihydro-4-quinolones bearing chiral tetrasubstituted carbons from isatins and 2′-aminoacetophenones. The transformation is mediated by a chiral phosphoric acid catalyst and proceeds via an <i>in situ</i> generated ketimine and subsequent enantioselective intramolecular cyclization. The methodology features a broad scope and functional group tolerance with yields and enantioselectivities of up to 99% and 98% ee. Detailed density functional theory (DFT) calculations support the proposed reaction mechanism and the origin of asymmetric induction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880226","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 three-component reaction of trifluoromethyl enones, phosphine oxides, and alcohols in water solution is developed. This defluorinative reaction occurs through a cascade process involving defluorophosphorylation, defluoroalkyloxylation, and defluoroheteroannulation, enabling the modular synthesis of furans with four distinct substituents: C2-alkyloxy, C3-trifluoromethyl, C4-phosphoryl, and C5-(hetero)aryl groups. Moreover, apart from alcohol substrates, the scope of nucleophiles could be further extended to phenols, azacycles, or sulfonamide.
{"title":"Modular Synthesis of Furans with Four Nonidentical Substituents by Aqueous Defluorinative Reaction of Trifluoromethyl Enones with Two Nucleophiles","authors":"Xue-Ying Huang, Shu-Ji Gao, Danhua Ge, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu","doi":"10.1021/acs.orglett.4c04488","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04488","url":null,"abstract":"A three-component reaction of trifluoromethyl enones, phosphine oxides, and alcohols in water solution is developed. This defluorinative reaction occurs through a cascade process involving defluorophosphorylation, defluoroalkyloxylation, and defluoroheteroannulation, enabling the modular synthesis of furans with four distinct substituents: <i>C</i>2-alkyloxy, <i>C</i>3-trifluoromethyl, <i>C</i>4-phosphoryl, and <i>C</i>5-(hetero)aryl groups. Moreover, apart from alcohol substrates, the scope of nucleophiles could be further extended to phenols, azacycles, or sulfonamide.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"42 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142884466","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}
Pub Date : 2024-12-24DOI: 10.1021/acs.orglett.4c04202
Xin Xie, Teng Gao, Shaogang Shen, Zhi Pang, Yuanyuan Qin, Xinyi Lv, Ying Wang
To experimentally investigate the impact of macrocyclic structures on the nonradiative decay rate constants (knrs) of thermally activated delayed fluorescence (TADF), a macrocyclic molecule L-ring and its analogue NL-ring were designed and synthesized. The photophysical measurements reveal their TADF characteristics, and the knrs of the L-ring (4.19 × 106 s–1) is slower than that of the NL-ring (1.96 × 107 s–1), endowing the L-ring with a photoluminescence quantum yield of 92.00%. Therefore, the L-ring device exhibited a high external quantum efficiency of 25.61%.
{"title":"Suppression of Nonradiative Decay in TADF Emitters via a Macrocyclic Strategy: An Experimental Study","authors":"Xin Xie, Teng Gao, Shaogang Shen, Zhi Pang, Yuanyuan Qin, Xinyi Lv, Ying Wang","doi":"10.1021/acs.orglett.4c04202","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04202","url":null,"abstract":"To experimentally investigate the impact of macrocyclic structures on the nonradiative decay rate constants (<i>k</i><sub>nr</sub><sup>s</sup>) of thermally activated delayed fluorescence (TADF), a macrocyclic molecule L-ring and its analogue NL-ring were designed and synthesized. The photophysical measurements reveal their TADF characteristics, and the <i>k</i><sub>nr</sub><sup>s</sup> of the L-ring (4.19 × 10<sup>6</sup> s<sup>–1</sup>) is slower than that of the NL-ring (1.96 × 10<sup>7</sup> s<sup>–1</sup>), endowing the L-ring with a photoluminescence quantum yield of 92.00%. Therefore, the L-ring device exhibited a high external quantum efficiency of 25.61%.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142884767","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}
Pub Date : 2024-12-24DOI: 10.1021/acs.orglett.4c03675
Qiaolin Ji, Xingxing Wei, Shengkun Liu, Yudai Matsuda
PF1163A (1) is a fungal metabolite that inhibits sterol-C4-methyl oxidase. In this study, we identified the biosynthetic gene cluster of 1 and elucidated its biosynthetic pathway through heterologous expression experiments. Polyketide synthase–nonribosomal synthetase hybrid PfaA, which is responsible for the biosynthesis of PF1163A, harbors an unusual domain organization with tandem condensation (C) domains and a terminal condensation domain. Mutagenesis studies suggest that both C domains are required for the function of PfaA.
{"title":"Involvement of a Noncanonical Polyketide Synthase–Nonribosomal Peptide Synthetase Hybrid in the Biosynthesis of Sterol-C4-methyl Oxidase Inhibitor PF1163A","authors":"Qiaolin Ji, Xingxing Wei, Shengkun Liu, Yudai Matsuda","doi":"10.1021/acs.orglett.4c03675","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03675","url":null,"abstract":"PF1163A (<b>1</b>) is a fungal metabolite that inhibits sterol-C4-methyl oxidase. In this study, we identified the biosynthetic gene cluster of <b>1</b> and elucidated its biosynthetic pathway through heterologous expression experiments. Polyketide synthase–nonribosomal synthetase hybrid PfaA, which is responsible for the biosynthesis of PF1163A, harbors an unusual domain organization with tandem condensation (C) domains and a terminal condensation domain. Mutagenesis studies suggest that both C domains are required for the function of PfaA.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142884768","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}
Pub Date : 2024-12-23DOI: 10.1021/acs.orglett.4c03623
Kaiming Zuo, Jing Zhu, Faral Akhtar, Phong Dam, Luis Miguel Azofra, Osama El-Sepelgy
Herein we present photoinduced cobaloxime-catalyzed selective remote desaturation of aliphatic alcohols. This transformation, which proceeds efficiently at room temperature, facilitates the synthesis of valuable cyclic and acyclic allylic and homoallylic alcohols from readily available saturated aliphatic alcohols. Remarkably, this method obviates the need for external oxidants, noble metal catalysts, and phosphine ligands.
{"title":"Biomimetic Catalytic Remote Desaturation of Aliphatic Alcohols","authors":"Kaiming Zuo, Jing Zhu, Faral Akhtar, Phong Dam, Luis Miguel Azofra, Osama El-Sepelgy","doi":"10.1021/acs.orglett.4c03623","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03623","url":null,"abstract":"Herein we present photoinduced cobaloxime-catalyzed selective remote desaturation of aliphatic alcohols. This transformation, which proceeds efficiently at room temperature, facilitates the synthesis of valuable cyclic and acyclic allylic and homoallylic alcohols from readily available saturated aliphatic alcohols. Remarkably, this method obviates the need for external oxidants, noble metal catalysts, and phosphine ligands.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874527","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}
Pub Date : 2024-12-23DOI: 10.1021/acs.orglett.4c04015
Zhao-Juan Wu, Ziyang Li, Yue Ren, Ling-Guo Meng
Recent advances in dual catalysis involving biomimetic conversion strategies that utilize radical ligand transfer (RLT) often rely on large doses of precious metal additives. The role of these additives within the mechanism remains ambiguous, leading to complex reaction conditions, uncertain pathways, and increased costs. These challenges complicate the study of the reaction process and are accompanied by potential safety risks. To address these issues, azide salt was used as an alternative to TMSN3. This replacement not only avoids the drawbacks associated with almost parallel research on alkene azidodifluoroalkylation but also eliminates the need for ligands. Comparative analysis indicates that existing biomimetic synergistic catalysis strategies require Ag2CO3 additives to enhance selectivity in alkene difunctionalization reactions, highlighting the superior simplicity, environmental friendliness, and operational ease of our developed synergistic catalysis strategy. Furthermore, under the guidance of our proposed mechanism, an alkene azidosulfonation was designed, validating the innovative and practical applicability of our synergistic catalysis approach.
{"title":"Overcoming Selectivity Trade-Offs in Alkene Azidodifluoroalkylation: An Enlightening Synergistic Catalytic Approach","authors":"Zhao-Juan Wu, Ziyang Li, Yue Ren, Ling-Guo Meng","doi":"10.1021/acs.orglett.4c04015","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04015","url":null,"abstract":"Recent advances in dual catalysis involving biomimetic conversion strategies that utilize radical ligand transfer (RLT) often rely on large doses of precious metal additives. The role of these additives within the mechanism remains ambiguous, leading to complex reaction conditions, uncertain pathways, and increased costs. These challenges complicate the study of the reaction process and are accompanied by potential safety risks. To address these issues, azide salt was used as an alternative to TMSN<sub>3</sub>. This replacement not only avoids the drawbacks associated with almost parallel research on alkene azidodifluoroalkylation but also eliminates the need for ligands. Comparative analysis indicates that existing biomimetic synergistic catalysis strategies require Ag<sub>2</sub>CO<sub>3</sub> additives to enhance selectivity in alkene difunctionalization reactions, highlighting the superior simplicity, environmental friendliness, and operational ease of our developed synergistic catalysis strategy. Furthermore, under the guidance of our proposed mechanism, an alkene azidosulfonation was designed, validating the innovative and practical applicability of our synergistic catalysis approach.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"6 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880125","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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