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Direct C4 and C2 C-H Amination of Heteroarenes Using I(III) Reagents via a Cross Azine Coupling. 使用 I(III)试剂通过交叉偶氮偶联法直接进行异戊二烯的 C4 和 C2 C-H 氨基化。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-08-28 DOI: 10.1021/acs.joc.4c01593
Bill J Motsch, Amelia H Quach, Jason L Dutton, David J D Wilson, Sarah E Wengryniuk
{"title":"Direct C4 and C2 C-H Amination of Heteroarenes Using I(III) Reagents via a Cross Azine Coupling.","authors":"Bill J Motsch, Amelia H Quach, Jason L Dutton, David J D Wilson, Sarah E Wengryniuk","doi":"10.1021/acs.joc.4c01593","DOIUrl":"10.1021/acs.joc.4c01593","url":null,"abstract":"<p><p>Aminated nitrogen heterocycles are valuable motifs across numerous chemical industries, perhaps most notably in small molecule drug discovery. While numerous strategies for installing nitrogen atoms onto azaarenes exist, most require prefunctionalization and methods for direct C-H amination are almost entirely limited to position C2. Herein, we report a method for the direct C2 and C4 C-H amination of fused azaarenes via <i>in situ</i> activation with a bispyridine-ligated I(III) reagent, [(Py)<sub>2</sub>IPh]2OTf, or <i>Py</i>-HVI. Unlike commonly used <i>N</i>-oxide chemistry, the method requires no preoxidation of the azaarene and provides unprecedented direct access to C4 amination products. The resulting N-heterocyclic pyridinium salts can be isolated via simple trituration. The free amine can be liberated under mild Zincke aminolysis, or the amination and cleavage can be telescoped to a one-pot process. The scope of the method is broad; the conditions are mild and operationally simple, and the aminated products are produced in good to excellent yields. Computational studies provide insights into the mechanism of activation, which involves an unusual direct nucleophilic functionalization of an I(III) ligand, as well as a kinetic basis for the observed C2 and C4 amination products.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142078431","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
Preparation of Difluoromethylated Benzothiophene by Visible-Light-Mediated Alkyne Difunctionalization Reaction. 通过可见光介导的炔烃二官能化反应制备二氟甲基化苯并噻吩。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-06 DOI: 10.1021/acs.joc.4c01528
Dong Zhang, Yu Sun, Ganwen Wang, Ying Liu, Chunjie Ni, Qingzhi Ji, Xiaojuan Xu, Zheng Fang
{"title":"Preparation of Difluoromethylated Benzothiophene by Visible-Light-Mediated Alkyne Difunctionalization Reaction.","authors":"Dong Zhang, Yu Sun, Ganwen Wang, Ying Liu, Chunjie Ni, Qingzhi Ji, Xiaojuan Xu, Zheng Fang","doi":"10.1021/acs.joc.4c01528","DOIUrl":"10.1021/acs.joc.4c01528","url":null,"abstract":"<p><p>An efficient method for the preparation of difluoromethylated benzothiophenes via visible-light-mediated alkyne difunctionalization was developed. In this method, inexpensive sodium difluoromethanesulfinate (HCF<sub>2</sub>SO<sub>2</sub>Na) was used as the fluorine source, and a variety of benzothiophene derivatives were obtained in moderate to excellent yield under mild reaction conditions. Moreover, the reaction operation is simple and easy to scale up.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138622","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
Base-Dependent Divergent Carbodifluoroalkylation and Halodifluoroalkylation of Alkenes under Visible-Light Irradiation. 可见光辐照下烯烃的碱依赖性歧化碳二氟烷基化和卤二氟烷基化反应。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-03 DOI: 10.1021/acs.joc.4c01591
Lin Tang, Fengjuan Jia, Lufang Zhang, Taijun Wu, Xinmeng Wei, Lingyun Zheng, Qiuju Zhou
{"title":"Base-Dependent Divergent Carbodifluoroalkylation and Halodifluoroalkylation of Alkenes under Visible-Light Irradiation.","authors":"Lin Tang, Fengjuan Jia, Lufang Zhang, Taijun Wu, Xinmeng Wei, Lingyun Zheng, Qiuju Zhou","doi":"10.1021/acs.joc.4c01591","DOIUrl":"10.1021/acs.joc.4c01591","url":null,"abstract":"<p><p>Organic molecules containing a difluoroalkyl group are valuable and versatile chemicals because of their unique physicochemical and biological properties. Accordingly, the development of efficient and practical difluoroalkylation for the preparation of these compounds is important and attractive. Herein, we demonstrate photoredox-catalyzed and base-dependent selective carbodifluoroalkylation and halodifluoroalkylation of alkenes using readily available 2-(allyloxy)arylaldehydes [or 2-(allylamino)arylaldehydes] and XCF<sub>2</sub>COOEt (or BrCF<sub>2</sub>CONR<sup>1</sup>R<sup>2</sup>) as starting materials. The developed reaction enables convenient and accurate synthesis of difluoroalkylated chroman-4-ones and aldehydes and features broad substrate scope, mild conditions, and operational simplicity. Moreover, gram-scale product preparation and application of the title protocol in late-stage functionalization of pharmaceutical molecules are accomplished.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118366","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
Gram-Scale Total Synthesis of Carbazomycins A-D through Late-Stage Regioselective Demethylation of Aryl Methyl Ethers. 通过后期芳基甲醚的区域选择性去甲基化，在革兰氏尺度上全合成咔唑霉素 A-D
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-05 DOI: 10.1021/acs.joc.4c01613
Yuxuan Feng, Atsunori Mori, Kentaro Okano
{"title":"Gram-Scale Total Synthesis of Carbazomycins A-D through Late-Stage Regioselective Demethylation of Aryl Methyl Ethers.","authors":"Yuxuan Feng, Atsunori Mori, Kentaro Okano","doi":"10.1021/acs.joc.4c01613","DOIUrl":"10.1021/acs.joc.4c01613","url":null,"abstract":"<p><p>Gram-scale total synthesis of carbazomycins A-D is described. The total synthesis of carbazomycin A was achieved in 44% overall yield over six steps from symmetrical 5-chloro-1,2,3-trimethoxybenzene. The key aryne-mediated carbazole formation and methylation steps provided the multiply substituted carbazole. The regioselective demethylation of the trimethoxycarbazole was performed using boron trichloride. Thereafter, the phenolic hydroxy group was converted into the methyl group to provide carbazomycin A. Subsequent installation of the methoxy group realized the total synthesis of carbazomycin D. Regioselective demethylation was performed using 1-dodecanethiol, effecting the conversions of carbazomycins A and D into carbazomycins B and C, respectively.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131199","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
Substituent-Oriented Synthesis of Substituted Pyridines/Pyrido[3,2-C]coumarins via Sequential Reactions of α-H and Me/Aryl Substituted Oxime Acetates and 3-Formylchromones. 以取代基为导向，通过 α-H 和 Me/Aryl 取代的肟醋酸酯与 3-Formylchromones 的顺序反应合成取代的吡啶/吡啶并[3,2-C]香豆素。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-08-28 DOI: 10.1021/acs.joc.4c00899
Varaprasad Bodala, Rajitha Lakshmi Podugu, Kumari Yettula, Sunanda Kumari Kadiri, Siddaiah Vidavalur
{"title":"Substituent-Oriented Synthesis of Substituted Pyridines/Pyrido[3,2-C]coumarins <i>via</i> Sequential Reactions of α-H and Me/Aryl Substituted Oxime Acetates and 3-Formylchromones.","authors":"Varaprasad Bodala, Rajitha Lakshmi Podugu, Kumari Yettula, Sunanda Kumari Kadiri, Siddaiah Vidavalur","doi":"10.1021/acs.joc.4c00899","DOIUrl":"10.1021/acs.joc.4c00899","url":null,"abstract":"<p><p>A facile one pot sequential and highly chemoselective synthesis of substituted pyridines/pyrido[3,2-<i>c</i>]coumarins has been developed from oxime acetates and 3-formylchromones in the presence of FeCl<sub>2</sub>. This reaction was oriented by different substituents on the α-position (H, methyl/aryl) of oxime acetates. Mechanistic investigations suggested that substituted pyridines were formed via intramolecular aza-Michael addition followed by ring opening, while pyrido[3,2-<i>c</i>]coumarins were formed via intermolecular Michael addition. Besides, anti-TB activity was screened for some of the synthesized pyridines. Among the tested compounds, <b>3ga</b>, <b>3ha</b>, <b>3ja</b>, <b>3ma</b>, <b>3ac</b>, <b>4pa</b>, <b>4pb</b> and <b>4sb</b> were found to have good activity with an MIC of 12.5 μg/mL.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142085895","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
Ammonium-Binding Bifunctional Aza-Crown Ether Catalysts for Substrate-Selective Hydroxyl Functionalization. 用于底物选择性羟基官能化的铵结合双功能氮冠醚催化剂。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-04 DOI: 10.1021/acs.joc.4c01498
Austin G Seilkop, Amaechi S Odoh, Nicholas J Coradi, Jacob I Wright, Jorge Barroso, Byoungmoo Kim
{"title":"Ammonium-Binding Bifunctional Aza-Crown Ether Catalysts for Substrate-Selective Hydroxyl Functionalization.","authors":"Austin G Seilkop, Amaechi S Odoh, Nicholas J Coradi, Jacob I Wright, Jorge Barroso, Byoungmoo Kim","doi":"10.1021/acs.joc.4c01498","DOIUrl":"10.1021/acs.joc.4c01498","url":null,"abstract":"<p><p>Herein, we describe a new bifunctional macrocyclic catalyst that employs multiple weak noncovalent interactions to enable substrate-selective O-silylation of ammonium alcohols over more reactive aliphatic alcohols with up to >20:1 substrate selectivity. Our catalytic strategy merges (i) the use of crown ethers as ammonium-binding receptors and (ii) the exploitation of <i>N</i>-methyl imidazole as a catalytic motif. Our collective mechanistic studies reveal the importance of receptor size, conformational preorganization, and the number of hydrogen-bonding acceptor units needed to achieve high selectivity within the macrocyclic binding pocket.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142124214","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
Catalyst-Free, Three-Component Synthesis of Amidinomaleimides. 无催化剂、三组分合成脒基马来酰亚胺。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-08-23 DOI: 10.1021/acs.joc.4c01485
Wyatt R Swift-Ramirez, Lindsay A Whalen, Lia K Thompson, Kaylee E Shoemaker, Aris V Rubio, Gregory A Weiss
{"title":"Catalyst-Free, Three-Component Synthesis of Amidinomaleimides.","authors":"Wyatt R Swift-Ramirez, Lindsay A Whalen, Lia K Thompson, Kaylee E Shoemaker, Aris V Rubio, Gregory A Weiss","doi":"10.1021/acs.joc.4c01485","DOIUrl":"10.1021/acs.joc.4c01485","url":null,"abstract":"<p><p>Maleimide and amidine functionalities often appear in medicinal and natural product targets. We describe a catalyst-free, three-component coupling reaction for the synthesis of amidinomaleimides. This one-pot reaction fuses a broad range of secondary amines and aldehydes with azidomaleimides. The conditions are mild, simple, modular, high yielding, and amenable to aqueous solvents. Most reaction products can be sufficiently purified without column chromatography. The synthesis creates complex, multifunctional molecules with four different molecules, including a tripeptide, arrayed around an amidinomaleimide core.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142043789","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
Scorpion-Shaped Hybrid Double Helicenes via Orthogonal Alkyne Annulation Reactions. 通过正交炔烃嵌合反应实现蝎形杂化双螺旋烯。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-09 DOI: 10.1021/acs.joc.4c01180
Mengyu Yao, Yaru Jing, Hongyan Bi, Zhuofeng Ke, Sunewang R Wang
{"title":"Scorpion-Shaped Hybrid Double Helicenes via Orthogonal Alkyne Annulation Reactions.","authors":"Mengyu Yao, Yaru Jing, Hongyan Bi, Zhuofeng Ke, Sunewang R Wang","doi":"10.1021/acs.joc.4c01180","DOIUrl":"10.1021/acs.joc.4c01180","url":null,"abstract":"<p><p>Scorpion-shaped hybrid double helicenes, consisting of a [5] or [6] carbohelicene and an aza[4]helicene, have been successfully constructed by orthogonal alkyne annulations via an aryl C-I bond and amido N-H bond from polyaromatic ring-fused iodoisocoumarins. In spite of the unexpected instability upon aerobic oxidation upon ambient visible light irradiation over several days, both ultraviolet-visible absorption and photoluminescence spectra along with density functional theory calculations of these helicenes have been studied, which rely heavily on the bent polyaromatic ring-fused quinolizinone conjugate skeleton. In addition, the Stokes shifts of hybrid double helicenes are generally larger than those of the structurally similar mono-carbohelicenes.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152469","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
TBD-Mediated Diastereoselective Access to Functionalized 3-Alkenyl-2-oxindoles via the Tandem Reaction of Isatins and Allenoates 通过异汀和烯酸盐的串联反应，以 TBD 为媒介非对映选择性地获得功能化的 3-烯基-2-吲哚
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 DOI: 10.1021/acs.joc.4c01427
Athira C. Santhoshkumar, Basavaraja Durugappa, Geethu Venugopal, Mohan Banyangala, Ajay Krishna M. S, Sasidhar B. Somappa
{"title":"TBD-Mediated Diastereoselective Access to Functionalized 3-Alkenyl-2-oxindoles via the Tandem Reaction of Isatins and Allenoates","authors":"Athira C. Santhoshkumar, Basavaraja Durugappa, Geethu Venugopal, Mohan Banyangala, Ajay Krishna M. S, Sasidhar B. Somappa","doi":"10.1021/acs.joc.4c01427","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01427","url":null,"abstract":"The 1,5,7-triazabicyclo[4.4.0]dec-5-ene–mediated tandem reaction of easily accessible isatins and allenoates to functionalized 3-alkenyl-2-oxindoles is disclosed. The reaction allows the synthesis of a wide range of 3-alkenyl-2-oxindoles in good yields with excellent functional group tolerance under mild reaction conditions (32 examples, up to 84% yields). The current strategy will provide a novel path for the sustainable synthesis of functionalized 3-alkenyl-2-oxindole derivatives. We have also demonstrated the significance of 3-alkenyl-2-oxindoles as key starting materials (KSMs) via their synthetic utility in producing oxindole-appended pyrazole, oxazole, and coumarin hybrids of medicinal relevance.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142273613","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
“Marriage” of Inorganic to Organic Chemistry as Motivation for a Theoretical Study of Chloroform Hydrolysis Mechanisms 无机化学与有机化学的 "联姻 "是氯仿水解机理理论研究的动因
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 DOI: 10.1021/acs.joc.4c00942
Christina Stamou, Spyros P. Perlepes, Michail M. Sigalas, Dionissios Papaioannou, Athanassios C. Tsipis, Evangelos G. Bakalbassis
{"title":"“Marriage” of Inorganic to Organic Chemistry as Motivation for a Theoretical Study of Chloroform Hydrolysis Mechanisms","authors":"Christina Stamou, Spyros P. Perlepes, Michail M. Sigalas, Dionissios Papaioannou, Athanassios C. Tsipis, Evangelos G. Bakalbassis","doi":"10.1021/acs.joc.4c00942","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00942","url":null,"abstract":"Incorporation of chlorides in coordination complexes, prepared by reactions in CHCl<sub>3</sub>, stimulated MP2 and DFT studies of its complete hydrolysis mechanisms. In excellent agreement with previous experimental results, the most important mechanism for CHCl<sub>3</sub> basic hydrolysis at room temperature is the radical one producing :CCl<sub>2</sub>. The latter inserts into the H–O bond of H<sub>2</sub>O yielding dichloromethanol (<b>1</b>). The hydrolysis mechanism of α-H-lacking PhCCl<sub>3</sub> to the corresponding dichloro(phenyl)methanol (<b>3</b>) was also studied. <b>1</b> decomposes by H<sub>2</sub>O to formyl chloride (<b>2</b>) and HCl. <b>2</b>, following a variety of pathways, leads to known CHCl<sub>3</sub> hydrolysis products, such as CO (<b>4</b>) and formic acid (<b>6</b>), via the intermediates chloromethanediol (<b>5</b>), <i>s-cis</i>, <i>s-trans</i>-dihydroxycarbene (<b>ct</b>-<b>7</b>), and <i>s</i>-<i>trans</i>, <i>s</i>-<i>trans</i>-dihydroxycarbene (<b>tt-7</b>). Interestingly, both <b>ct</b>-<b>7</b> and <b>tt-7</b> intermediates have recently been implicated in the reduction of CO<sub>2</sub> with H<sub>2</sub> to <b>6</b>. The conversion of CO to HCOOH was studied. Most of the reactions studied are asynchronous concerted processes, the radical mechanism being a multistep one. The synthetic utility of this mechanism is briefly mentioned. To avoid chloride ions when performing reactions in CHCl<sub>3</sub>, we should use the solvent at room temperature even in the presence of water. This has been verified further by coordination chemistry reactions in progress.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247223","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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