Pub Date : 2025-03-06DOI: 10.1021/acs.orglett.5c00283
Shahida Perveen, Tariq Ali, Tahir Rahman, Fatima Noor Ul Huda, Lingyun Wang, Junjie Zhang, Ajmal Khan
The first enantioconvergent transition-metal-catalyzed amination of racemic α-tertiary 1,2-diols providing access to vicinal β-amino α-tertiary alcohols is disclosed. The iridium-catalyzed amination reaction proceeds through a chiral phosphoric acid-mediated borrowing hydrogen pathway with excellent yields and enantioselectivities for a range of amine nucleophiles and α-tertiary 1,2-diols. An array of β-amino α-tertiary alcohols were obtained with high yields and enantioselectivities (50 examples with up to 91% yield and up to 99% ee). These important chiral amino alcohol products can be easily converted into chiral ligands and bioactive skeletons. Mechanistic investigations proposed a dynamic kinetic resolution pathway involving imine formation and then imine reduction as the enantiodetermining step.
{"title":"Catalytic Asymmetric Synthesis of β-Amino α-Tertiary Alcohol through Borrowing Hydrogen Amination","authors":"Shahida Perveen, Tariq Ali, Tahir Rahman, Fatima Noor Ul Huda, Lingyun Wang, Junjie Zhang, Ajmal Khan","doi":"10.1021/acs.orglett.5c00283","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00283","url":null,"abstract":"The first enantioconvergent transition-metal-catalyzed amination of racemic α-tertiary 1,2-diols providing access to vicinal β-amino α-tertiary alcohols is disclosed. The iridium-catalyzed amination reaction proceeds through a chiral phosphoric acid-mediated borrowing hydrogen pathway with excellent yields and enantioselectivities for a range of amine nucleophiles and α-tertiary 1,2-diols. An array of β-amino α-tertiary alcohols were obtained with high yields and enantioselectivities (50 examples with up to 91% yield and up to 99% ee). These important chiral amino alcohol products can be easily converted into chiral ligands and bioactive skeletons. Mechanistic investigations proposed a dynamic kinetic resolution pathway involving imine formation and then imine reduction as the enantiodetermining step.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143570328","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 : 2025-03-06DOI: 10.1021/acs.orglett.5c00209
David R. Williams, Fese M. Okha, Sarah A. Ward
A convergent route toward the synthesis of leiodolide A (1) is described. Our studies explored reactions of the indium chloride-induced transmetalation of allylic stannane 32 for nucleophilic addition with nonracemic aldehyde 15. The stereoselective formation of the all-syn stereotriad was rationalized by an in situ isomerization to produce the Z-allylindium reagent for subsequent anti-Felkin addition. The inversion of C17 stereochemistry led to an effective π-allyl Stille cross coupling utilizing Z-alkenylstannane 11b. The Horner–Wadsworth–Emmons reaction provides macrolactone 37 which exhibits discrepancies as compared with reported NMR data for the purported leiodolide A.
{"title":"Synthesis of Leiodolide A Macrolactone","authors":"David R. Williams, Fese M. Okha, Sarah A. Ward","doi":"10.1021/acs.orglett.5c00209","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00209","url":null,"abstract":"A convergent route toward the synthesis of leiodolide A (<b>1</b>) is described. Our studies explored reactions of the indium chloride-induced transmetalation of allylic stannane <b>32</b> for nucleophilic addition with nonracemic aldehyde <b>15</b>. The stereoselective formation of the all-<i>syn</i> stereotriad was rationalized by an <i>in situ</i> isomerization to produce the <i>Z</i>-allylindium reagent for subsequent <i>anti</i>-Felkin addition. The inversion of C<sub>17</sub> stereochemistry led to an effective π-allyl Stille cross coupling utilizing <i>Z</i>-alkenylstannane <b>11b</b>. The Horner–Wadsworth–Emmons reaction provides macrolactone <b>37</b> which exhibits discrepancies as compared with reported NMR data for the purported leiodolide A.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"36 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561264","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 : 2025-03-06DOI: 10.1021/acs.orglett.5c00697
Ziming Wu, Zehai Lu, Yongrui Luo, Linhua Wang, Matthew Hughes, Stephen Smith, Zhuang Hou, Qilong Shen
CF3CCl2-containing compounds are of significant synthetic value but are typically synthesized from environmentally harmful hydrochlorofluorocarbons (CFCs). Herein, we report the use of a well-defined Cu(I) complex, [(bpy)Cu(CF3)], as an efficient trifluoromethylating reagent for the direct trifluoromethylation of trichloroalkanes under mild conditions, affording CF3CCl2-containing products with excellent chemoselectivity. This protocol also enabled the gram-scale synthesis of cyhalothric acid ester, which is a key intermediate in the production of pyrethroid pesticides.
{"title":"Copper-Mediated Direct Trifluoromethylation of Trichloromethyl Alkanes","authors":"Ziming Wu, Zehai Lu, Yongrui Luo, Linhua Wang, Matthew Hughes, Stephen Smith, Zhuang Hou, Qilong Shen","doi":"10.1021/acs.orglett.5c00697","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00697","url":null,"abstract":"CF<sub>3</sub>CCl<sub>2</sub>-containing compounds are of significant synthetic value but are typically synthesized from environmentally harmful hydrochlorofluorocarbons (CFCs). Herein, we report the use of a well-defined Cu(I) complex, [(bpy)Cu(CF<sub>3</sub>)], as an efficient trifluoromethylating reagent for the direct trifluoromethylation of trichloroalkanes under mild conditions, affording CF<sub>3</sub>CCl<sub>2</sub>-containing products with excellent chemoselectivity. This protocol also enabled the gram-scale synthesis of cyhalothric acid ester, which is a key intermediate in the production of pyrethroid pesticides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"50 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561267","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}
C–C bond cleavage reactions have achieved remarkable progress in molecular deconstruction and skeleton editing. In this study, we describe a palladium-catalyzed synthesis of diaryl ketones through a sequence of α-arylation and aerobic oxidative C–C bond cleavage. This transformation features good functional group compatibility, especially for highly reactive groups, including −OH, NH2, and −CHO. Furthermore, this approach allows for gram-scale synthesis in a low catalyst loading manner. It also streamlines the synthesis of a variety of drugs or their intermediates. Mechanism studies reveal the essential role of utilizing a bulky ligand and the existence of air as the reaction atmosphere.
{"title":"Palladium-Catalyzed C(O)–C Bond Cleavage of Unstrained Ketones Assisted with Aryl Handles: An Approach to Diaryl Ketones","authors":"Qiang Li, Yang Long, Qinyue Tao, Zewei Jin, Xufei Yan, Xiangge Zhou","doi":"10.1021/acs.orglett.5c00455","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00455","url":null,"abstract":"C–C bond cleavage reactions have achieved remarkable progress in molecular deconstruction and skeleton editing. In this study, we describe a palladium-catalyzed synthesis of diaryl ketones through a sequence of α-arylation and aerobic oxidative C–C bond cleavage. This transformation features good functional group compatibility, especially for highly reactive groups, including −OH, NH<sub>2</sub>, and −CHO. Furthermore, this approach allows for gram-scale synthesis in a low catalyst loading manner. It also streamlines the synthesis of a variety of drugs or their intermediates. Mechanism studies reveal the essential role of utilizing a bulky ligand and the existence of air as the reaction atmosphere.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"58 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561265","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 : 2025-03-06DOI: 10.1021/acs.orglett.5c00574
Bai-Hui Zhang, Lu Gan, Yu-Wei Wu, Wen-Xian Li, Dean Guo, Wei Li
Alpinoblonoids A (1) and B (2), two 16-nor-labdane related diterpenoids featuring 2,6,6,10,11-pentamethyltricyclo[8.4.0.02,7]tetradecane and 11-ethyl-2,6,6,10-tetramethyltricyclo[8.3.0.02,7]tridecane skeletons, respectively, along with their biosynthetic precursor (3), were isolated from the rhizomes of Alpinia oblongifolia. Their structural elucidation was achieved by a variety of techniques, including spectroscopic and chemical methods, ECD calculations, as well as single-crystal X-ray diffraction. Compounds 1 and 2 exhibited antihepatic fibrosis activity by inhibiting the expressions of fibronectin, collagen I, and α-smooth muscle actin.
{"title":"Alpinoblonoids A and B, Two 16-nor-Labdane-Related Diterpenoids with a Tricyclic Carbon Skeleton from Alpinia oblongifolia","authors":"Bai-Hui Zhang, Lu Gan, Yu-Wei Wu, Wen-Xian Li, Dean Guo, Wei Li","doi":"10.1021/acs.orglett.5c00574","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00574","url":null,"abstract":"Alpinoblonoids A (<b>1</b>) and B (<b>2</b>), two 16-<i>nor</i>-labdane related diterpenoids featuring 2,6,6,10,11-pentamethyltricyclo[8.4.0.0<sup>2,7</sup>]tetradecane and 11-ethyl-2,6,6,10-tetramethyltricyclo[8.3.0.0<sup>2,7</sup>]tridecane skeletons, respectively, along with their biosynthetic precursor (<b>3</b>), were isolated from the rhizomes of <i>Alpinia oblongifolia</i>. Their structural elucidation was achieved by a variety of techniques, including spectroscopic and chemical methods, ECD calculations, as well as single-crystal X-ray diffraction. Compounds <b>1</b> and <b>2</b> exhibited antihepatic fibrosis activity by inhibiting the expressions of fibronectin, collagen I, and α-smooth muscle actin.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"53 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561266","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 : 2025-03-06DOI: 10.1021/acs.orglett.5c00503
Wangyang Li, Yong Lu, Shanshan Cheng, Qiuling Song
Herein, we report a novel palladium(II)-initiated borono-Catellani reaction that utilizes widely accessible aryl boronic acids that serve as both the reaction-initiating and -terminating substrates for the first time. The borono-Catellani reaction was facilitated by cooperative catalysis between Pd(OAc)2 and NBE, with air serving as the oxidizing agent, opening new venues for developing novel Catellani-type reactions. Importantly, this method is compatible with a wide range of substrates, including naphthaleneboronic acid, phenylboric acid derivatives, alkyl iodides, and aryl iodides, under these environmentally friendly and mild reaction conditions, thereby demonstrating versatile functional group compatibility for the synthesis of valuable polysubstituted aromatics.
{"title":"Synthesis of Polysubstituted Aromatics via the Pd(II)-Initiated Borono-Catellani Reaction","authors":"Wangyang Li, Yong Lu, Shanshan Cheng, Qiuling Song","doi":"10.1021/acs.orglett.5c00503","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00503","url":null,"abstract":"Herein, we report a novel palladium(II)-initiated borono-Catellani reaction that utilizes widely accessible aryl boronic acids that serve as both the reaction-initiating and -terminating substrates for the first time. The borono-Catellani reaction was facilitated by cooperative catalysis between Pd(OAc)<sub>2</sub> and NBE, with air serving as the oxidizing agent, opening new venues for developing novel Catellani-type reactions. Importantly, this method is compatible with a wide range of substrates, including naphthaleneboronic acid, phenylboric acid derivatives, alkyl iodides, and aryl iodides, under these environmentally friendly and mild reaction conditions, thereby demonstrating versatile functional group compatibility for the synthesis of valuable polysubstituted aromatics.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143570331","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 : 2025-03-06DOI: 10.1021/acs.orglett.5c00593
Natasha F. M. Ansarian, Liam T. Ball
We report a new C–O arylation strategy for the synthesis of 2-arylphenols from bio-abundant guaiacols. Functionalization of the strong C–O bond is achieved through a sequence of arylative dearomatization, mediated selectively by an electrophilic bismuth(V) arylating agent, followed by 1,2-reduction and deoxygenative rearomatization. This methodology represents a rare example of complexity-generating deoxygenation applied to lignin-derived biorefinery feedstocks and provides independence from the regioselectivity rules established for the bismuth(V)-mediated arylation of simple phenols.
{"title":"Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C–O Arylation of Guaiacols","authors":"Natasha F. M. Ansarian, Liam T. Ball","doi":"10.1021/acs.orglett.5c00593","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00593","url":null,"abstract":"We report a new C–O arylation strategy for the synthesis of 2-arylphenols from bio-abundant guaiacols. Functionalization of the strong C–O bond is achieved through a sequence of arylative dearomatization, mediated selectively by an electrophilic bismuth(V) arylating agent, followed by 1,2-reduction and deoxygenative rearomatization. This methodology represents a rare example of complexity-generating deoxygenation applied to lignin-derived biorefinery feedstocks and provides independence from the regioselectivity rules established for the bismuth(V)-mediated arylation of simple phenols.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"52 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143570332","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 : 2025-03-05DOI: 10.1021/acs.orglett.5c00476
Runze Zhai, Haiping Yu, Jiexiang Ma, Yaxin Sun, Peng Yang
A controlled cleavage of double C–F bonds in sterically hindered tetrasubstituted CF3-alkenes using formate salt has been achieved through a photoinduced electron transfer approach. Diverse γ-branched multifunctionalized gem-difluoroalkenes and α-fluoroacrylic acids are obtained sequentially via hydrodefluorination and C–F bond carboxylation with good-to-high yields. Precisely controlling the quantity of formate salt and the reaction time is crucial for obtaining divergent defluorinative products. Formate serves as the C1 source, hydrogen donor, and reducing agent.
{"title":"Controlled Defluorinative Carboxylation Cascade of Sterically Hindered CF3-Alkenes with Formate Salt via Photocatalysis","authors":"Runze Zhai, Haiping Yu, Jiexiang Ma, Yaxin Sun, Peng Yang","doi":"10.1021/acs.orglett.5c00476","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00476","url":null,"abstract":"A controlled cleavage of double C–F bonds in sterically hindered tetrasubstituted CF<sub>3</sub>-alkenes using formate salt has been achieved through a photoinduced electron transfer approach. Diverse γ-branched multifunctionalized <i>gem</i>-difluoroalkenes and α-fluoroacrylic acids are obtained sequentially via hydrodefluorination and C–F bond carboxylation with good-to-high yields. Precisely controlling the quantity of formate salt and the reaction time is crucial for obtaining divergent defluorinative products. Formate serves as the C1 source, hydrogen donor, and reducing agent.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"36 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143546662","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 : 2025-03-05DOI: 10.1021/acs.orglett.5c00631
Yu Hong, Jun Xu, An Chen, Yating Du, Guangze Wang, Jiabin Shen, Pengfei Zhang
Herein, we introduce an efficient and straightforward strategy for the selective C–H esterification and alkylation of quinoxalin-2(1H)-ones with aldehydes. A key feature of our study is the ability to perform both C–H esterification and alkylation using different types of aldehydes. The reaction system is highly compatible with a range of quinoxalin-2(1H)-ones and aldehydes, yielding C3-esterified and C3-alkylated products in moderate-to-good yields. The applicability of this approach is further enhanced by its scalability through continuous-flow synthesis, late-stage modification of significant molecules, and product derivatization. Our mechanistic investigations reveal a radical relay mechanism, triggered by a hydrogen atom transfer process.
{"title":"Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions","authors":"Yu Hong, Jun Xu, An Chen, Yating Du, Guangze Wang, Jiabin Shen, Pengfei Zhang","doi":"10.1021/acs.orglett.5c00631","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00631","url":null,"abstract":"Herein, we introduce an efficient and straightforward strategy for the selective C–H esterification and alkylation of quinoxalin-2(1<i>H</i>)-ones with aldehydes. A key feature of our study is the ability to perform both C–H esterification and alkylation using different types of aldehydes. The reaction system is highly compatible with a range of quinoxalin-2(1<i>H</i>)-ones and aldehydes, yielding C3-esterified and C3-alkylated products in moderate-to-good yields. The applicability of this approach is further enhanced by its scalability through continuous-flow synthesis, late-stage modification of significant molecules, and product derivatization. Our mechanistic investigations reveal a radical relay mechanism, triggered by a hydrogen atom transfer process.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"131 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143546664","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 : 2025-03-05DOI: 10.1021/acs.orglett.5c00208
David R. Williams, Fese M. Okha, Sarah A. Ward
Studies have described a highly convergent plan toward the synthesis of leiodolide A (1), a potent cytotoxic sponge metabolite. The enantiocontrolled preparation of aldehyde 6 is achieved with the application of several advances in methodology for the synthesis of substituted 1,3-oxazoles. Efforts have examined the halogen dance reaction, the selectivity of Stille cross coupling reactions of 4-bromo-1,3-oxazoles, and nucleophilic displacement of the 2-phenylsulfonyl substituent with organolithium reagents as preparatively useful reactions. These techniques have facilitated the efficient synthesis of 6 from the starting bromide 12, alkenylstannane 16, and the primary nonracemic alcohol 25.
{"title":"Studies Toward the Synthesis of Leiodolide A","authors":"David R. Williams, Fese M. Okha, Sarah A. Ward","doi":"10.1021/acs.orglett.5c00208","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00208","url":null,"abstract":"Studies have described a highly convergent plan toward the synthesis of leiodolide A (<b>1</b>), a potent cytotoxic sponge metabolite. The enantiocontrolled preparation of aldehyde <b>6</b> is achieved with the application of several advances in methodology for the synthesis of substituted 1,3-oxazoles. Efforts have examined the halogen dance reaction, the selectivity of Stille cross coupling reactions of 4-bromo-1,3-oxazoles, and nucleophilic displacement of the 2-phenylsulfonyl substituent with organolithium reagents as preparatively useful reactions. These techniques have facilitated the efficient synthesis of <b>6</b> from the starting bromide <b>12</b>, alkenylstannane <b>16</b>, and the primary nonracemic alcohol <b>25</b>.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561209","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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