Pub Date : 2025-02-18DOI: 10.1021/acs.orglett.5c00021
Priyankar Jha, Saddam Husen, Ravindra Kumar
Reported here is a catalytic redox-neutral geminal dual C–H functionalization of oxindoles with two distinct aromatics using anilines. The reaction proceeded through a pluripotent tetra-substituted alkene intermediate via an extended resonance stabilized carbocation. It furnished wide chemical space around oxindoles with the generation of all carbon quaternary centers (>35 examples) in good to excellent yields. The developed process is highly regioselective and scalable, and the conditions are environmentally benign in nature.
{"title":"Building an All Carbon Quaternary Center via Redox-Neutral Geminal Dual C–H Functionalization of Oxindoles","authors":"Priyankar Jha, Saddam Husen, Ravindra Kumar","doi":"10.1021/acs.orglett.5c00021","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00021","url":null,"abstract":"Reported here is a catalytic redox-neutral geminal dual C–H functionalization of oxindoles with two distinct aromatics using anilines. The reaction proceeded through a pluripotent tetra-substituted alkene intermediate via an extended resonance stabilized carbocation. It furnished wide chemical space around oxindoles with the generation of all carbon quaternary centers (>35 examples) in good to excellent yields. The developed process is highly regioselective and scalable, and the conditions are environmentally benign in nature.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435695","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 : 2025-02-18DOI: 10.1021/acs.orglett.4c04603
Yi-Ying Du, Yu-Shi He, Yan Liang, Xue-Song Liu, Juan Liu, Long-Hui Gai, Shang-Zhong Liu, Yi-Ming Cao
We report a chiral phosphoric acid-catalyzed hydrolytic parallel kinetic resolution (HPKR) of racemic epoxides and activated alcohols. Using an acyloxy-assisted activation strategy, this method enables the highly stereocontrolled hydrolysis under mild conditions. A wide range of aryl-substituted epoxides and activated secondary alcohols were effectively transformed, providing corresponding chiral alcohols with combined yields of up to 99% and enantiomeric ratios exceeding 99:1.
{"title":"Chiral Phosphoric Acid-Catalyzed Hydrolytic Parallel Kinetic Resolution of Racemic Epoxides and Activated Alcohols","authors":"Yi-Ying Du, Yu-Shi He, Yan Liang, Xue-Song Liu, Juan Liu, Long-Hui Gai, Shang-Zhong Liu, Yi-Ming Cao","doi":"10.1021/acs.orglett.4c04603","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04603","url":null,"abstract":"We report a chiral phosphoric acid-catalyzed hydrolytic parallel kinetic resolution (HPKR) of racemic epoxides and activated alcohols. Using an acyloxy-assisted activation strategy, this method enables the highly stereocontrolled hydrolysis under mild conditions. A wide range of aryl-substituted epoxides and activated secondary alcohols were effectively transformed, providing corresponding chiral alcohols with combined yields of up to 99% and enantiomeric ratios exceeding 99:1.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435537","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 : 2025-02-18DOI: 10.1021/acs.orglett.5c00148
Zeynep Saglam, Shuyu Liu, Yiding Chen, Loïc R. E. Pantaine, Matthew G. Lloyd, Aaron J. Senior
An intramolecular cyclization strategy to synthesize nitrogen-rich and biologically important 2-heteroaryl-indolin-3-ones has been developed in both batch and flow. Using high-throughput screening, citric acid in a dimethylformamide/water mixture was found to facilitate the reaction under batch conditions, which can tolerate substituted phenyl rings, quinolines, and naphthalenes with a variety of electronic and steric properties. The reaction was reoptimized for flow conditions using design of experiments, complementing the batch conditions for some substrates with greatly reduced reaction times.
{"title":"Preparation of 2-Heteroaryl-indolin-3-ones by Acid-Mediated Intramolecular Cyclization in Batch and Flow","authors":"Zeynep Saglam, Shuyu Liu, Yiding Chen, Loïc R. E. Pantaine, Matthew G. Lloyd, Aaron J. Senior","doi":"10.1021/acs.orglett.5c00148","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00148","url":null,"abstract":"An intramolecular cyclization strategy to synthesize nitrogen-rich and biologically important 2-heteroaryl-indolin-3-ones has been developed in both batch and flow. Using high-throughput screening, citric acid in a dimethylformamide/water mixture was found to facilitate the reaction under batch conditions, which can tolerate substituted phenyl rings, quinolines, and naphthalenes with a variety of electronic and steric properties. The reaction was reoptimized for flow conditions using design of experiments, complementing the batch conditions for some substrates with greatly reduced reaction times.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"64 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435538","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 : 2025-02-18DOI: 10.1021/acs.orglett.5c00415
Xiaonan Mu, Yulong Niu, Minhui Guan, Hao Chen, Chuan-Ying Li, Lei Wang
In the published manuscript, a related paper should be cited as ref 13(c): Xiao, K.; Luo, J.; Ye, K.; Wang, Y.; Huang, P. Direct, One-pot Sequential Reductive Alkylation of Lactams/Amides with Grignard and Organolithium Reagents through Lactam/Amide Activation. Angew. Chem., Int. Ed.2010, 49, 3037–3040 10.1002/anie.201000652. This article has not yet been cited by other publications.
{"title":"Correction to “Reaction of Donor–Acceptor α-Diazo Esters and N,N-Dimethylformamide/γ-Lactams to Generate α-Amino-α-aroylethanoates”","authors":"Xiaonan Mu, Yulong Niu, Minhui Guan, Hao Chen, Chuan-Ying Li, Lei Wang","doi":"10.1021/acs.orglett.5c00415","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00415","url":null,"abstract":"In the published manuscript, a related paper should be cited as ref 13(c): <contrib-group person-group-type=\"allauthors\"><span>Xiao, K.</span>; <span>Luo, J.</span>; <span>Ye, K.</span>; <span>Wang, Y.</span>; <span>Huang, P.</span></contrib-group> Direct, One-pot Sequential Reductive Alkylation of Lactams/Amides with Grignard and Organolithium Reagents through Lactam/Amide Activation. <cite><i>Angew. Chem., Int. Ed.</i></cite> <span>2010</span>, <em>49</em>, 3037–3040 10.1002/anie.201000652</pub-id>. This article has not yet been cited by other publications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435539","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 : 2025-02-17DOI: 10.1021/acs.orglett.5c00174
Jia-Cheng Li, Jia-Wang Li, Rui Zhang, Dewen Dong
A straightforward synthesis of α-oxoketene N,X-acetals (X = O, S, or N) from β-oxoamides has been described. The oxyphosphonium intermediates are quickly generated in situ from β-oxoamides in the presence of Hendrickson reagent and triflic anhydride (Tf2O) in a chemoselective manner and undergo a chemoselective nucleophilic substitution with phenols, thiophenols, or aromatic amines to deliver the desired products with high stereoselectivity. The one-pot synthetic protocol features readily available starting materials, mild conditions, simple execution, and a wide range of synthetic potentials of the products.
{"title":"Highly Stereoselective Synthesis of α-Oxoketene N,X-Acetals (X = O, S, or N) under Mild Conditions","authors":"Jia-Cheng Li, Jia-Wang Li, Rui Zhang, Dewen Dong","doi":"10.1021/acs.orglett.5c00174","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00174","url":null,"abstract":"A straightforward synthesis of α-oxoketene <i>N,X</i>-acetals (<i>X</i> = O, S, or N) from β-oxoamides has been described. The oxyphosphonium intermediates are quickly generated <i>in situ</i> from β-oxoamides in the presence of Hendrickson reagent and triflic anhydride (Tf<sub>2</sub>O) in a chemoselective manner and undergo a chemoselective nucleophilic substitution with phenols, thiophenols, or aromatic amines to deliver the desired products with high stereoselectivity. The one-pot synthetic protocol features readily available starting materials, mild conditions, simple execution, and a wide range of synthetic potentials of the products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435541","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 : 2025-02-17DOI: 10.1021/acs.orglett.5c00192
Yuanmin Wen, Teng Liu, Shuntao Huang, Guiyun Zeng, Zhou Zhang, Yanqing Ye, Chao Huang
We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing a wide scope of structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 examples, 74–86% yields), and 1,4-thiazines (6 examples, 31–68% yields). The characteristics of this transformation are high atomic economy, formation of two C–Se or C–S bonds in one step, and avoiding the use of unstable and toxic selenium/sulfur reagents under mild conditions.
{"title":"Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes","authors":"Yuanmin Wen, Teng Liu, Shuntao Huang, Guiyun Zeng, Zhou Zhang, Yanqing Ye, Chao Huang","doi":"10.1021/acs.orglett.5c00192","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00192","url":null,"abstract":"We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing a wide scope of structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 examples, 74–86% yields), and 1,4-thiazines (6 examples, 31–68% yields). The characteristics of this transformation are high atomic economy, formation of two C–Se or C–S bonds in one step, and avoiding the use of unstable and toxic selenium/sulfur reagents under mild conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427289","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 : 2025-02-17DOI: 10.1021/acs.orglett.5c00102
Lin Xiao, Zhiqiang Wei, Chuanfa Ni, Alexander D. Dilman, Jinbo Hu
Molecules containing fluoroalkyl and arylthio groups play a pivotal role in pharmaceutical and agrochemical development. The simultaneous introduction of these functional groups through the 1,2-difunctionalization of alkenes is an efficient strategy. Fluoroalkyl phenyl sulfones serve as accessible fluoroalkyl radical precursors; however, their tendency to interact with thiophenol via the electron donor–acceptor interaction mechanism can impede the desired transformation. Through meticulous selection of solvent and base, we successfully utilized copper catalysis to facilitate an alkene-involved three-component reaction. Our work unveils a photoredox copper-catalyzed fluoroalkylation–thiolation of alkenes using various fluoroalkyl phenyl sulfones (such as perfluoroethyl, tetrafluoroethyl, trifluoromethyl, difluoromethyl, difluoroalkyl, and difluorobenzyl). The efficacy of this approach is exemplified by the synthesis of Kengreal derivatives.
{"title":"From S-Fluoroalkylation to Fluoroalkylation–Thiolation: Difunctionalization of Alkenes with Fluoroalkyl Phenyl Sulfones and Thiophenols Enabled by Photoredox Copper Catalysis","authors":"Lin Xiao, Zhiqiang Wei, Chuanfa Ni, Alexander D. Dilman, Jinbo Hu","doi":"10.1021/acs.orglett.5c00102","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00102","url":null,"abstract":"Molecules containing fluoroalkyl and arylthio groups play a pivotal role in pharmaceutical and agrochemical development. The simultaneous introduction of these functional groups through the 1,2-difunctionalization of alkenes is an efficient strategy. Fluoroalkyl phenyl sulfones serve as accessible fluoroalkyl radical precursors; however, their tendency to interact with thiophenol via the electron donor–acceptor interaction mechanism can impede the desired transformation. Through meticulous selection of solvent and base, we successfully utilized copper catalysis to facilitate an alkene-involved three-component reaction. Our work unveils a photoredox copper-catalyzed fluoroalkylation–thiolation of alkenes using various fluoroalkyl phenyl sulfones (such as perfluoroethyl, tetrafluoroethyl, trifluoromethyl, difluoromethyl, difluoroalkyl, and difluorobenzyl). The efficacy of this approach is exemplified by the synthesis of Kengreal derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"137 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427287","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 palladium-catalyzed Heck-type cross-coupling reaction of carboranes with alkenes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was realized. This reaction shows good B(9) selectivity for m-carboranes and is also suitable for o- and p-carborane. Meanwhile, a series of mono-, di-, and trisubstituted alkenes were compatible substrates to afford the alkenylated products in 16–89% yields. The 1,2-bis(carboranyl)ethylene was first synthesized by the reaction of vinyltrimethylsilane and m-carborane. Further transformations of the C═C bond in the product were examined by hydroboration oxidation, oxidation, hydroboration, and bromination reaction to generate corresponding B(9)-functionalized m-carboranes.
{"title":"Palladium-Catalyzed Cross-Coupling Reactions of Carboranes with Alkenes via Selective B–H Bond Activation","authors":"Jia-Rui Chang, Hou-Ji Cao, Yan-Na Ma, Xuenian Chen","doi":"10.1021/acs.orglett.5c00059","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00059","url":null,"abstract":"A palladium-catalyzed Heck-type cross-coupling reaction of carboranes with alkenes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was realized. This reaction shows good B(9) selectivity for <i>m</i>-carboranes and is also suitable for <i>o</i>- and <i>p</i>-carborane. Meanwhile, a series of mono-, di-, and trisubstituted alkenes were compatible substrates to afford the alkenylated products in 16–89% yields. The 1,2-bis(carboranyl)ethylene was first synthesized by the reaction of vinyltrimethylsilane and <i>m</i>-carborane. Further transformations of the C═C bond in the product were examined by hydroboration oxidation, oxidation, hydroboration, and bromination reaction to generate corresponding B(9)-functionalized <i>m</i>-carboranes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427286","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 have achieved racemization of axially chiral diamines such as 1,1′-binaphthyl-2,2′-diamine (BINAM) by utilizing a visible-light-driven single-electron oxidation. BINAM derivatives were racemized at 30–40 °C via blue-light irradiation in the presence of an Ir(dF(CF3)ppy)2(dtbpy)PF6 photocatalyst and N,N-dimethylaniline to afford racemic BINAM in 99% yield with <1% ee. Mechanistic studies demonstrated that the photocatalyst promoted the oxidation of BINAM to generate a radical cation species to facilitate racemization at low temperatures. Subsequent single-electron reduction by dimethylaniline afforded racemic BINAM. Dynamic kinetic resolution was also achieved with 80% enantioselectivity through a combination of kinetic resolution and racemization.
{"title":"Visible-Light-Driven Racemization of 1,1′-Binaphthyl-2,2′-diamine (BINAM) Derivatives","authors":"Tatsuhiro Uchikura, Mikoto Sato, Yuki Kanno, Yukino Fukuda, Yurina Hara, Kota Yamamoto, Takahiko Akiyama","doi":"10.1021/acs.orglett.5c00162","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00162","url":null,"abstract":"We have achieved racemization of axially chiral diamines such as 1,1′-binaphthyl-2,2′-diamine (BINAM) by utilizing a visible-light-driven single-electron oxidation. BINAM derivatives were racemized at 30–40 °C via blue-light irradiation in the presence of an Ir(dF(CF<sub>3</sub>)ppy)<sub>2</sub>(dtbpy)PF<sub>6</sub> photocatalyst and <i>N,N-</i>dimethylaniline to afford racemic BINAM in 99% yield with <1% ee. Mechanistic studies demonstrated that the photocatalyst promoted the oxidation of BINAM to generate a radical cation species to facilitate racemization at low temperatures. Subsequent single-electron reduction by dimethylaniline afforded racemic BINAM. Dynamic kinetic resolution was also achieved with 80% enantioselectivity through a combination of kinetic resolution and racemization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"49 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427288","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 : 2025-02-17DOI: 10.1021/acs.orglett.5c00285
Cong Huang, Zhen-Zhen Xie, Jie Gao, Mei Xiang, Hao-Yue Xiang, Kai Chen, Hua Yang
A metal-free photosensitized 1,2-imino-thiocyanation of olefins has been established by using the easily accessible bifunctional reagent S-cyano-N-(diphenylmethylene) thiohydroxylamine. A wide range of olefins were successfully transformed into the corresponding β-iminothiocyanates in moderate to high yields. This protocol stands out for its metal-free nature, broad substrate compatibility, and high atom and step economy, providing an effective strategy for assembling β-amino thiocyanate-containing scaffolds.
{"title":"Photosensitized Imino-Thiocyanation of Alkenes","authors":"Cong Huang, Zhen-Zhen Xie, Jie Gao, Mei Xiang, Hao-Yue Xiang, Kai Chen, Hua Yang","doi":"10.1021/acs.orglett.5c00285","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00285","url":null,"abstract":"A metal-free photosensitized 1,2-imino-thiocyanation of olefins has been established by using the easily accessible bifunctional reagent <i>S</i>-cyano-<i>N</i>-(diphenylmethylene) thiohydroxylamine. A wide range of olefins were successfully transformed into the corresponding β-iminothiocyanates in moderate to high yields. This protocol stands out for its metal-free nature, broad substrate compatibility, and high atom and step economy, providing an effective strategy for assembling β-amino thiocyanate-containing scaffolds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"85 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427315","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}