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Dual Nickel- and Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling To Access Chiral Secondary Benzylic Alcohols. 镍和光氧化催化的不对称还原交叉偶联获得手性仲苄基醇。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-02-07 DOI: 10.1021/acs.joc.3c02293
Shun Wen, Jie Bu, Kun Shen
{"title":"Dual Nickel- and Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling To Access Chiral Secondary Benzylic Alcohols.","authors":"Shun Wen, Jie Bu, Kun Shen","doi":"10.1021/acs.joc.3c02293","DOIUrl":"10.1021/acs.joc.3c02293","url":null,"abstract":"<p><p>Transition-metal-catalyzed asymmetric cross-coupling represents a powerful strategy for C-C bond formation and the synthesis of enantiomerically pure molecules. Here, we report a dual nickel/photoredox-catalyzed enantioselective reductive cross-coupling of aryl halides with α-bromobenzoates, readily generated from aliphatic aldehydes, to provide diverse chiral secondary benzylic alcohols that are important motifs in bioactive natural products and pharmaceuticals. This dual catalytic system features mild conditions, good functional group tolerance, broad substrate scope, excellent enantiocontrol, and avoidance of stoichiometric metal reductants, presenting great potential for late-stage functionalization of complex molecules.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16134-16144"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139701246","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Concise Synthesis of (2R,6R)-Hydroxynorketamine. (2R,6R)-羟基炔诺酮胺的简明合成。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-01 DOI: 10.1021/acs.joc.4c01502
Jianfeng Li, Ankun Zhou, Xiaoting Wang, Wenping Zhang, Qixin Zhou, Ning Li
{"title":"A Concise Synthesis of (<i>2R,6R</i>)-Hydroxynorketamine.","authors":"Jianfeng Li, Ankun Zhou, Xiaoting Wang, Wenping Zhang, Qixin Zhou, Ning Li","doi":"10.1021/acs.joc.4c01502","DOIUrl":"10.1021/acs.joc.4c01502","url":null,"abstract":"<p><p>A concise synthesis of (<i>2R,6R</i>)-hydroxynorketamine was accomplished in eight steps, starting from commercially available materials. This synthesis features a cerium chloride-enhanced Stork-Danheiser reaction, an asymmetric reduction of ketone by the Corey-Bakshi-Shibata reaction, a signature Overman rearrangement, and a facial selective dihydroxylation of an electronically deficient olefin by RuCl<sub>3</sub>/NaIO<sub>4</sub>. The overall yield is 7.3% with 94.5% <i>ee</i>.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16909-16916"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556654","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide. 从磺酰胺制备磺酰亚胺基氟化物的快速、温和且直接的途径。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-30 DOI: 10.1021/acs.joc.4c01644
Padma Priya V R, Antony Haritha Mercy A, Natarajan K, Sugapriya S, Ganesh Chandra Nandi
{"title":"A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide.","authors":"Padma Priya V R, Antony Haritha Mercy A, Natarajan K, Sugapriya S, Ganesh Chandra Nandi","doi":"10.1021/acs.joc.4c01644","DOIUrl":"10.1021/acs.joc.4c01644","url":null,"abstract":"<p><p>We develop a rapid and mild protocol to access sulfonimidoyl fluoride-[S(VI)] from sulfenamide-[S(II)] directly. The transformation occurs via the reaction of sulfenamide with NCS (<i>N</i>-chlorosuccinimide), water, and TBAF in acetonitrile. Water and TBAF act as the source for S═O bond formation and fluoride, respectively. The reaction takes a very short time (within 5 min). The drug molecules, such as Carbamazepine and Levetiracetam attached sulfonimidoyl fluorides are also achieved following this protocol. Furthermore, sulfonimidoyl fluoride is transformed into sulfonimidamide in the presence of AlCl<sub>3</sub>. To the best of our knowledge, it is the first report detailing the synthesis of sulfonimidoyl fluoride-[S(VI)] directly from S(II)-sulfenamide.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16426-16432"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542911","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of 2-Amino-4-arylazulenes from 8-Aryl-2H-cyclohepta[b]furan-2-ones and Transformation into 6-Aryl-7H-naphth[3,2,1-cd]azulen-7-ones. 从 8-芳基-2H-环庚烷并[b]呋喃-2-酮合成 2-氨基-4-芳基偶氮烯并转化为 6-芳基-7H-萘并[3,2,1-cd]偶氮烯-7-酮。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-04 DOI: 10.1021/acs.joc.4c01394
Taku Shoji, Daichi Ando, Masayuki Iwabuchi, Atom Hamasaki, Shigeki Mori, Tetsuo Okujima, Ryuta Sekiguchi, Shunji Ito
{"title":"Synthesis of 2-Amino-4-arylazulenes from 8-Aryl-2<i>H</i>-cyclohepta[<i>b</i>]furan-2-ones and Transformation into 6-Aryl-7<i>H</i>-naphth[3,2,1-<i>cd</i>]azulen-7-ones.","authors":"Taku Shoji, Daichi Ando, Masayuki Iwabuchi, Atom Hamasaki, Shigeki Mori, Tetsuo Okujima, Ryuta Sekiguchi, Shunji Ito","doi":"10.1021/acs.joc.4c01394","DOIUrl":"10.1021/acs.joc.4c01394","url":null,"abstract":"<p><p>2-Amino-4-arylazulene derivatives were prepared from 8-aryl-2<i>H</i>-cyclohepta[<i>b</i>]furan-2-ones, which were converted into 6-aryl-7<i>H</i>-naphth[3,2,1-<i>cd</i>]azulen-7-ones through a several step process. The reaction of 8-aryl-2<i>H</i>-cyclohepta[<i>b</i>]furan-2-ones bearing an ester group at the 3-position with malononitrile in the presence of triethylamine afforded 2-amino-4-arylazulenes. The prepared 2-amino-4-arylazulenes were converted to the corresponding 2-chloro derivatives by the Sandmeyer reaction, which were subsequently transformed into 2,4-diarylazulenes by Suzuki-Miyaura coupling with various aryl boronic acids. 2,4-Diarylazulenes underwent intramolecular cyclization between aryl and cyano groups by Brønsted acid to give 6-aryl-7<i>H</i>-naphth[3,2,1-<i>cd</i>]azulen-7-ones. UV/vis spectral analysis revealed that 6-aryl-7<i>H</i>-naphth[3,2,1-<i>cd</i>]azulen-7-one with a <i>N</i>,<i>N</i>-dimethylaminophenyl group at the 6-position exhibited a broad and strong absorption band in the visible region due to intramolecular charge transfer. Furthermore, 6-aryl-7<i>H</i>-naphth[3,2,1-<i>cd</i>]azulen-7-ones exhibited halochromism in 30% CF<sub>3</sub>CO<sub>2</sub>H/CH<sub>2</sub>Cl<sub>2</sub>. Although fluorescence was not observed in solution, 8-aryl-2<i>H</i>-cyclohepta[<i>b</i>]furan-2-ones with an ester function were found to fluoresce in the solid state. 6-Aryl-7<i>H</i>-naphth[3,2,1-<i>cd</i>]azulen-7-ones also displayed spectral changes with good reversibility under the electrochemical redox conditions.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16375-16389"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142566426","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nickel-Catalyzed Reductive Arylation of Redox Active Esters for the Synthesis of α-Aryl Nitriles: Investigation of a Chlorosilane Additive. 镍催化氧化还原活性酯的还原芳基化反应以合成 α-芳基腈：氯硅烷添加剂的研究。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-01-10 DOI: 10.1021/acs.joc.3c02354
Nicholas W M Michel, Alexis L Gabbey, Racquel K Edjoc, Emmanuel Fagbola, Jonathan M E Hughes, Louis-Charles Campeau, Sophie A L Rousseaux
{"title":"Nickel-Catalyzed Reductive Arylation of Redox Active Esters for the Synthesis of α-Aryl Nitriles: Investigation of a Chlorosilane Additive.","authors":"Nicholas W M Michel, Alexis L Gabbey, Racquel K Edjoc, Emmanuel Fagbola, Jonathan M E Hughes, Louis-Charles Campeau, Sophie A L Rousseaux","doi":"10.1021/acs.joc.3c02354","DOIUrl":"10.1021/acs.joc.3c02354","url":null,"abstract":"<p><p>A nickel-catalyzed reductive cross-coupling of redox active <i>N</i>-hydroxyphthalimide (NHP) esters and iodoarenes for the synthesis of α-aryl nitriles is described. The NHP ester substrate is derived from cyanoacetic acid, which allows for a modular synthesis of substituted α-aryl nitriles, an important scaffold in the pharmaceutical sciences. The reaction exhibits a broad scope, and many functional groups are compatible under the reaction conditions, including complex highly functionalized medicinal agents. Mechanistic studies reveal that reduction and decarboxylation of the NHP ester to the reactive radical intermediate are accomplished by a combination of a chlorosilane additive and Zn dust. We demonstrate that stoichiometric chlorosilane is essential for product formation and that chlorosilane plays a role beyond activation of the metal reductant.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16161-16169"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139400997","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
2-Halomethyleneoxetanes from 2-Methyleneoxetanes by Reaction with N-Halosuccinimides: Reactant Influences on Stereochemical Outcomes and Reaction Pathways. 通过与 N-卤代丁二酰亚胺反应制备 2-亚甲基氧杂环丁烷：反应物对立体化学结果和反应途径的影响。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-05 DOI: 10.1021/acs.joc.4c01877
Dennis Sulwey, Julia B DiSapio, José A Gascón, Amy R Howell
{"title":"2-Halomethyleneoxetanes from 2-Methyleneoxetanes by Reaction with <i>N</i>-Halosuccinimides: Reactant Influences on Stereochemical Outcomes and Reaction Pathways.","authors":"Dennis Sulwey, Julia B DiSapio, José A Gascón, Amy R Howell","doi":"10.1021/acs.joc.4c01877","DOIUrl":"10.1021/acs.joc.4c01877","url":null,"abstract":"<p><p>The first general synthesis of 2-halomethyleneoxetanes, realized by the reaction of 2-methyleneoxetanes with <i>N</i>-halosuccinimides (NXS), is reported. The relative diastereoselectivities of the transformations were dependent on the halogen of NXS, while alternative reaction outcomes were influenced by substituents on the oxetane. Quantum mechanical calculations and molecular dynamics simulations exploring the basis of the observed diastereoselectivities are described. These highly strained heterocycles underwent standard cross-coupling reactions, demonstrating their utility as synthetic intermediates.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16571-16585"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142580912","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Leveraging the Redox Promiscuity of Nickel To Catalyze C-N Coupling Reactions. 利用镍的氧化还原性催化 C-N 偶联反应
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-01-17 DOI: 10.1021/acs.joc.3c02353
Olivia R Taylor, Paul J Saucedo, Ana Bahamonde
{"title":"Leveraging the Redox Promiscuity of Nickel To Catalyze C-N Coupling Reactions.","authors":"Olivia R Taylor, Paul J Saucedo, Ana Bahamonde","doi":"10.1021/acs.joc.3c02353","DOIUrl":"10.1021/acs.joc.3c02353","url":null,"abstract":"<p><p>This perspective details advances made in the field of Ni-catalyzed C-N bond formation. The use of this Earth abundant metal to decorate amines, amides, lactams, and heterocycles enables direct access to a variety of biologically active and industrially relevant compounds in a sustainable manner. Herein, different strategies that leverage the propensity of Ni to facilitate both one- and two-electron processes will be surveyed. The first part of this Perspective focuses on strategies that facilitate C-N couplings at room temperature by accessing oxidized Ni(III) intermediates. In this context, advances in photochemical, electrochemical, and chemically mediated processes will be analyzed. A special emphasis has been put on providing a comprehensive explanation of the different mechanistic avenues that have been proposed to facilitate these chemistries; either Ni(I/III) self-sustained cycles or Ni(0/II/III) photochemically mediated pathways. The second part of this Perspective details the ligand designs that also enable access to this reactivity via a two-electron Ni(0/II) mechanism. Finally, we discuss our thoughts on possible future directions of the field.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16093-16105"},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139477604","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Metal-Hydride C-C Cross-Coupling of Alkenes Through a Double Outer-Sphere Mechanism. 通过双外球机制实现烯烃的金属氢化物 C-C 交叉偶联
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-06-26 DOI: 10.1021/acs.joc.4c00260
Nathan Dao, Xu-Cheng Gan, Ryan A Shenvi
{"title":"Metal-Hydride C-C Cross-Coupling of Alkenes Through a Double Outer-Sphere Mechanism.","authors":"Nathan Dao, Xu-Cheng Gan, Ryan A Shenvi","doi":"10.1021/acs.joc.4c00260","DOIUrl":"10.1021/acs.joc.4c00260","url":null,"abstract":"<p><p>This Synopsis covers recent reports of metal-catalyzed alkene functionalizations that likely involve iterative outer-sphere reactions in which the substrate reacts directly with a metal ligand instead of with the metal center itself. Traditional metal hydride-catalyzed alkene functionalizations involve this latter pathway whereby the alkene forms part of the metal ligand sphere (i.e. an inner-sphere reaction). In contrast, alkenes do not ligate the metal in so-called outer-sphere reactions and instead react with a metal ligand. These transformations have proved crucial for the synthesis of high fraction sp<sup>3</sup> (F<sub>sp</sub>3) targets, especially in hindered fragment couplings of relevance to natural product space.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16106-16113"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453758","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoredox-Catalyzed Three-Component Construction of Aryl Sulfonyl Fluoride Using KHF2: Late-Stage Drug Fluorosulfonylation. 利用 KHF2 光氧化催化三组分构建芳基磺酰氟：后期药物氟磺酰化。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-01 DOI: 10.1021/acs.joc.4c01892
Hanhan Sun, Wanqing Meng, Xiaoxu Ma, Zhiling Cheng, Cheng Chen, Yan Ni, Fengying Yan, Qiaomei Zhu, Ping Zhang, Xianwei Sui
{"title":"Photoredox-Catalyzed Three-Component Construction of Aryl Sulfonyl Fluoride Using KHF<sub>2</sub>: Late-Stage Drug Fluorosulfonylation.","authors":"Hanhan Sun, Wanqing Meng, Xiaoxu Ma, Zhiling Cheng, Cheng Chen, Yan Ni, Fengying Yan, Qiaomei Zhu, Ping Zhang, Xianwei Sui","doi":"10.1021/acs.joc.4c01892","DOIUrl":"10.1021/acs.joc.4c01892","url":null,"abstract":"<p><p>Aryl sulfonyl fluorides are prominently featured in organic synthesis and medicinal chemistry. Herein, a metal-free photoredox-catalyzed three-component assembly of aryl sulfonyl fluoride via aryl sulfonyl ammonium salt intermediate has been reported. A variety of structurally diverse aryl sulfonyl fluorides were synthesized rapidly from dibenzothiophenium (DBT) salts under mild conditions by using KHF<sub>2</sub> as the fluorine source. Notably, this methodology can be employed as an efficient and sustainable approach for late-stage drug fluorosulfonylation. Good yields and broad functionality tolerance were the features of this methodology. Moreover, the derivatization of aryl sulfonyl fluoride molecules was also demonstrated to showcase its synthetic utility.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16594-16599"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556660","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Interrupted Michael Reaction: Sulfophosphinoylation of α,β-Unsaturated Ketones Catalyzed by Phosphine. 间断迈克尔反应：磷催化的 α、β-不饱和酮的硫代磷酰化反应。
IF 4.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-30 DOI: 10.1021/acs.joc.4c01860
Xiao-Hong Wei, Ya-Wen Xue, Xuan Liu, Xiao-Hong Wang, Yan-Bin Wang, Qiong Su
{"title":"Interrupted Michael Reaction: Sulfophosphinoylation of α,β-Unsaturated Ketones Catalyzed by Phosphine.","authors":"Xiao-Hong Wei, Ya-Wen Xue, Xuan Liu, Xiao-Hong Wang, Yan-Bin Wang, Qiong Su","doi":"10.1021/acs.joc.4c01860","DOIUrl":"10.1021/acs.joc.4c01860","url":null,"abstract":"<p><p>An efficient method for phosphine-catalyzed sulfophosphinoylation of α,β-unsaturated ketones for synthesis allylic organophosphorus compounds has been reported, in which α,β-unsaturated compounds acting as zwitterions react with electrophiles and nucleophiles to form a C-P bond and a C-O bond and obtain allylic organophosphorus with high regio- and stereoselectivity in moderate to excellent yields.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16564-16570"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542914","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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