Herein, we disclosed a dual-functionalization of tryptophan derivatives at the C2 and C4 positions of the indole ring through a palladium-catalyzed cascade C–H activation. This step-economical protocol features operational simplicity under mild conditions, achieving concurrent aryl and acetoxy group installation in one pot, making it a straightforward approach to efficiently synthesize highly decorated tryptophan derivatives. Furthermore, gram-scale synthesis and further transformation were also feasible, demonstrating the robustness of this method.
{"title":"One-pot C2-arylation and C4-acetoxylation of tryptophan derivatives via palladium-catalyzed tandem C–H activation†","authors":"Jia-Tian Liu , Jiashu Liu , Qi-Long Hu , Jian Li","doi":"10.1039/d5qo00671f","DOIUrl":"10.1039/d5qo00671f","url":null,"abstract":"<div><div>Herein, we disclosed a dual-functionalization of tryptophan derivatives at the C2 and C4 positions of the indole ring through a palladium-catalyzed cascade C–H activation. This step-economical protocol features operational simplicity under mild conditions, achieving concurrent aryl and acetoxy group installation in one pot, making it a straightforward approach to efficiently synthesize highly decorated tryptophan derivatives. Furthermore, gram-scale synthesis and further transformation were also feasible, demonstrating the robustness of this method.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5591-5596"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144488799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kemeng Zhang , Shuodan Ding , Jie Zhou , Xinyu Zhou , Ge Wu , XinLei Wu
Bunte salts are frequently utilized as effective thiolation reagents for constructing thioethers. In this study, we discovered that Bunte salts could also serve as mediators to enable the oxidative C–H sulfonation of alkenes with sodium sulfinates. Mechanistically, alkyl sulfides are generated as key intermediates, which undergo an unusual oxidative elimination to give the corresponding products. These tandem addition–elimination reactions allow for the conversion of various styrenes and α-alkyl styrenes into vinyl and allylic sulfones in useful to excellent yields.
{"title":"Bunte salt-mediated sulfonation of alkenes with sodium sulfinates†","authors":"Kemeng Zhang , Shuodan Ding , Jie Zhou , Xinyu Zhou , Ge Wu , XinLei Wu","doi":"10.1039/d5qo00618j","DOIUrl":"10.1039/d5qo00618j","url":null,"abstract":"<div><div>Bunte salts are frequently utilized as effective thiolation reagents for constructing thioethers. In this study, we discovered that Bunte salts could also serve as mediators to enable the oxidative C–H sulfonation of alkenes with sodium sulfinates. Mechanistically, alkyl sulfides are generated as key intermediates, which undergo an unusual oxidative elimination to give the corresponding products. These tandem addition–elimination reactions allow for the conversion of various styrenes and α-alkyl styrenes into vinyl and allylic sulfones in useful to excellent yields.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5616-5621"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144341381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In recent years, radical-mediated functionalization of olefins has gradually become a research hotspot in the field of organic synthesis due to its high reactivity, excellent regioselectivity, and wide substrate applicability. Compared to traditional ionic pathways, radical strategies effectively avoid compatibility issues with some functional groups through modes, such as photocatalysis, electrocatalysis, or chemical initiation, and provide new pathways for the diversified conversion of olefins, such as bifunctional, hydrogen functionalization, and cyclization reactions. Among them, tert-butyl hydroperoxide (TBHP) plays multiple roles in synthetic chemistry as an efficient and inexpensive oxidant and radical precursor: it is not only a classic initiator of radical chain reactions but also a source of tert-butyl peroxide, tert-butyl oxygen, methyl, oxygen, hydrogen, or hydroxyl groups. The unique capacity to generate controllable radical species establishes TBHP as an indispensable platform for advancing green synthetic methodologies, empowering pharmaceutical innovation and deciphering fundamental reaction mechanisms. In this review, we summarize the recent progress in TBHP-enabled transformations of alkenes, which are categorized as peroxidation, carbonylation, epoxidation, etherification, hydrogenation, and hydroxylation. Within each category, representative studies are presented and discussed in terms of mechanistic insights and substrate scope expansion.
{"title":"Radical di- and multi-functionalization of alkenes: recent advances in diverse reaction modes utilizing TBHP as reactants","authors":"Jiantao Zhang , Renhua Su , Weibing Liu","doi":"10.1039/d5qo00785b","DOIUrl":"10.1039/d5qo00785b","url":null,"abstract":"<div><div>In recent years, radical-mediated functionalization of olefins has gradually become a research hotspot in the field of organic synthesis due to its high reactivity, excellent regioselectivity, and wide substrate applicability. Compared to traditional ionic pathways, radical strategies effectively avoid compatibility issues with some functional groups through modes, such as photocatalysis, electrocatalysis, or chemical initiation, and provide new pathways for the diversified conversion of olefins, such as bifunctional, hydrogen functionalization, and cyclization reactions. Among them, <em>tert</em>-butyl hydroperoxide (TBHP) plays multiple roles in synthetic chemistry as an efficient and inexpensive oxidant and radical precursor: it is not only a classic initiator of radical chain reactions but also a source of <em>tert</em>-butyl peroxide, <em>tert</em>-butyl oxygen, methyl, oxygen, hydrogen, or hydroxyl groups. The unique capacity to generate controllable radical species establishes TBHP as an indispensable platform for advancing green synthetic methodologies, empowering pharmaceutical innovation and deciphering fundamental reaction mechanisms. In this review, we summarize the recent progress in TBHP-enabled transformations of alkenes, which are categorized as peroxidation, carbonylation, epoxidation, etherification, hydrogenation, and hydroxylation. Within each category, representative studies are presented and discussed in terms of mechanistic insights and substrate scope expansion.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5683-5716"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329438","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Boron-containing derivatives have numerous applications in medicinal, industrial, and synthetic chemistry. Considering this, a new, mild, catalyst-free, additive-free, base-assisted one-step robust method has been reported for the efficient synthesis of valuable 1,2-oxaborole derivatives via borylation of propynols using only cesium carbonate as a mild base. The reaction proceeds under mild conditions and demonstrates broad substrate scope and high functional group tolerance, making it suitable for a wide range of propargylic alcohols. Mechanistic investigations reveal that this method proceeds through a non-radical pathway.
{"title":"Synthesis of 1,2-oxaborole via base-mediated borylation of propynols†","authors":"Sumit Ghosh , Sudip Laru , Mukta Singsardar , Alakananda Hajra","doi":"10.1039/d5qo00709g","DOIUrl":"10.1039/d5qo00709g","url":null,"abstract":"<div><div>Boron-containing derivatives have numerous applications in medicinal, industrial, and synthetic chemistry. Considering this, a new, mild, catalyst-free, additive-free, base-assisted one-step robust method has been reported for the efficient synthesis of valuable 1,2-oxaborole derivatives <em>via</em> borylation of propynols using only cesium carbonate as a mild base. The reaction proceeds under mild conditions and demonstrates broad substrate scope and high functional group tolerance, making it suitable for a wide range of propargylic alcohols. Mechanistic investigations reveal that this method proceeds through a non-radical pathway.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5597-5602"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144334889","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chunxiao Nong , Kun He , Yingguo Jiang , Fan Zhu , Mingquan Yuan , Jingbo Chen , Yi Jin
Herein, we report a K2S2O8-mediated metal-free radical dehydrogenative cross-coupling reaction that achieves direct C(sp2)–H/C(sp3)–H radical–radical coupling between N,N-dimethylenaminones and glycine derivatives. This reaction efficiently proceeds under oxidative conditions via a single-electron transfer (SET) mechanism, generating both enaminone radicals and α-amino radicals for subsequent coupling. This methodology enables one-step synthesis of 31 structurally diverse 2,3-dicarbonylquinoline derivatives, including 2,3-benzoylquinolines, 2,3-diester quinolines, and 2-ester-3-acylquinolines. This protocol establishes a robust foundation for future applications of such 2,3-dicarbonylquinoline compounds.
{"title":"Cross-dehydrogenative radical coupling enabled by K2S2O8: efficient synthesis of 2,3-dicarbonyl quinolines from enaminones and glycine derivatives†","authors":"Chunxiao Nong , Kun He , Yingguo Jiang , Fan Zhu , Mingquan Yuan , Jingbo Chen , Yi Jin","doi":"10.1039/d5qo00677e","DOIUrl":"10.1039/d5qo00677e","url":null,"abstract":"<div><div>Herein, we report a K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated metal-free radical dehydrogenative cross-coupling reaction that achieves direct C(sp<sup>2</sup>)–H/C(sp<sup>3</sup>)–H radical–radical coupling between <em>N</em>,<em>N</em>-dimethylenaminones and glycine derivatives. This reaction efficiently proceeds under oxidative conditions <em>via</em> a single-electron transfer (SET) mechanism, generating both enaminone radicals and α-amino radicals for subsequent coupling. This methodology enables one-step synthesis of 31 structurally diverse 2,3-dicarbonylquinoline derivatives, including 2,3-benzoylquinolines, 2,3-diester quinolines, and 2-ester-3-acylquinolines. This protocol establishes a robust foundation for future applications of such 2,3-dicarbonylquinoline compounds.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5430-5437"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144177256","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Axel Leblond , Érick Caique Santos Costa , Karine Leblanc , Edmond Gravel , Jean-François Gallard , Mehdi A. Beniddir , Erwan Poupon
Haouamines are highly constrained marine alkaloids possessing a unique in nature skeleton. The high degree of complexity of such alkaloids raises questions about their chemical assembly. This is addressed in this paper in which we propose a biomimetic scenario corroborated experimentally by a fine study of the classical Chichibabin pyridine synthesis, especially in its “abnormal” oxidative version. Finely tuned reductive conditions and mechanistic investigations permit the concise obtention of an advanced and challenging intermediate that we coined “pre-haouamine”.
{"title":"Bypassing the abnormal Chichibabin reaction dead-end provides a biomimetic access to pre-haouamine","authors":"Axel Leblond , Érick Caique Santos Costa , Karine Leblanc , Edmond Gravel , Jean-François Gallard , Mehdi A. Beniddir , Erwan Poupon","doi":"10.1039/d5qo01111f","DOIUrl":"10.1039/d5qo01111f","url":null,"abstract":"<div><div>Haouamines are highly constrained marine alkaloids possessing a unique in nature skeleton. The high degree of complexity of such alkaloids raises questions about their chemical assembly. This is addressed in this paper in which we propose a biomimetic scenario corroborated experimentally by a fine study of the classical Chichibabin pyridine synthesis, especially in its “abnormal” <em>oxidative</em> version. Finely tuned <em>reductive</em> conditions and mechanistic investigations permit the concise obtention of an advanced and challenging intermediate that we coined “<em>pre</em>-haouamine”.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5372-5378"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145230119","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Siddhartha Kumar Senapati , Tapashi Das , Animesh Das
Hexafluoroisopropanol (HFIP)-mediated one-pot tandem reduction of quinolines to tetrahydroquinolines followed by reductive alkylation by the aldehyde has been demonstrated through H-bonding network-enabled substrate activation. This step-economical synthetic approach is well suited for late-stage functionalization of complex bioactive molecules. The reaction is highly chemoselective and tolerates a wide range of reducible-sensitive functional groups. The current reductive N-alkylation approach was also successfully utilized to synthesize novel tricyclic oxazino-fused-tetrahydroquinoline/benzoxazine compounds via tandem reductive cyclization of 1-aryl-2-(8-quinolinyloxy) ethanones and synthesis of lilolidine derivatives through the reductive N-alkylation of quinoline followed by a dehydration cyclization sequence. The scope of the reaction has been further extended to C-functionalized N-alkylated THQ derivatives in a one-pot by using para-quinone methides (p-QMs) or nitroolefins as alkylating precursors. The elucidation of an underlying mechanism was achieved through a combination of several control experiments, kinetic studies, and isotopic labeling experiments.
{"title":"Tandem reductive alkylation of quinolines to functionalized tetrahydroquinolines enabled by HFIP†","authors":"Siddhartha Kumar Senapati , Tapashi Das , Animesh Das","doi":"10.1039/d5qo00519a","DOIUrl":"10.1039/d5qo00519a","url":null,"abstract":"<div><div>Hexafluoroisopropanol (HFIP)-mediated one-pot tandem reduction of quinolines to tetrahydroquinolines followed by reductive alkylation by the aldehyde has been demonstrated through H-bonding network-enabled substrate activation. This step-economical synthetic approach is well suited for late-stage functionalization of complex bioactive molecules. The reaction is highly chemoselective and tolerates a wide range of reducible-sensitive functional groups. The current reductive <em>N</em>-alkylation approach was also successfully utilized to synthesize novel tricyclic oxazino-fused-tetrahydroquinoline/benzoxazine compounds <em>via</em> tandem reductive cyclization of 1-aryl-2-(8-quinolinyloxy) ethanones and synthesis of lilolidine derivatives through the reductive <em>N</em>-alkylation of quinoline followed by a dehydration cyclization sequence. The scope of the reaction has been further extended to <em>C</em>-functionalized <em>N</em>-alkylated THQ derivatives in a one-pot by using <em>para</em>-quinone methides (<em>p</em>-QMs) or nitroolefins as alkylating precursors. The elucidation of an underlying mechanism was achieved through a combination of several control experiments, kinetic studies, and isotopic labeling experiments.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5582-5590"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260760","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A facile bottom-up synthesis of a contorted polycyclic aromatic hydrocarbon (PAH) derivative is reported. The structure features three expanded heptagonal rings, constructed by structural extension of a tris-cycloheptenylene core with the integration of three anthraquinone units into the π-conjugated architecture. This strategy enables gram-scale synthesis with decent yields under mild conditions. Single crystal X-ray crystallographic analysis confirmed a saddle-shaped geometry induced by the three heptagons. This work provides a generalizable strategy for designing highly curved PAHs with tunable optoelectronic functionalities.
{"title":"Facile synthesis of a contorted polycyclic aromatic hydrocarbon derivative†","authors":"Xiaoxia Duan , Kai Lan , Yue Su , Chuyang Cheng","doi":"10.1039/d5qo00604j","DOIUrl":"10.1039/d5qo00604j","url":null,"abstract":"<div><div>A facile bottom-up synthesis of a contorted polycyclic aromatic hydrocarbon (PAH) derivative is reported. The structure features three expanded heptagonal rings, constructed by structural extension of a tris-cycloheptenylene core with the integration of three anthraquinone units into the π-conjugated architecture. This strategy enables gram-scale synthesis with decent yields under mild conditions. Single crystal X-ray crystallographic analysis confirmed a saddle-shaped geometry induced by the three heptagons. This work provides a generalizable strategy for designing highly curved PAHs with tunable optoelectronic functionalities.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5504-5510"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144211683","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Norbert Baris , Martin Dračínský , Luca Julianna Tóth , Blanka Klepetářová , Petr Beier
Trifluoromethyl nitrene generated photocatalytically from azidotrifluoromethane was added to sulfides to afford new N-trifluoromethylsulfilimines. Their methylation yielded N-methyl-N trifluoromethyl sulfonium salts and oxidation provided N-trifluoromethyl sulfoximines.
{"title":"Synthesis of N-trifluoromethylsulfilimines via trifluoromethyl nitrene and their synthetic potential†","authors":"Norbert Baris , Martin Dračínský , Luca Julianna Tóth , Blanka Klepetářová , Petr Beier","doi":"10.1039/d5qo00873e","DOIUrl":"10.1039/d5qo00873e","url":null,"abstract":"<div><div>Trifluoromethyl nitrene generated photocatalytically from azidotrifluoromethane was added to sulfides to afford new <em>N</em>-trifluoromethylsulfilimines. Their methylation yielded <em>N</em>-methyl-<em>N</em> trifluoromethyl sulfonium salts and oxidation provided <em>N</em>-trifluoromethyl sulfoximines.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5610-5615"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144479394","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dou Zhang , Peng Shen , Yao Zhang , Qiuyi Zheng , Jiahui Zhang , Chunyu Han , Silin Xu , Jinhua Yang
A TFPN (3,4,5,6-tetrafluorophthalonitrile)-mediated esterification strategy has been developed for the efficient synthesis of esters, thioesters, and macrolactones within remarkably short reaction times. Key to this approach is the utilization of in situ-generated acyl fluorides as transient intermediates, which circumvent stability limitations associated with conventional activated species. This method demonstrates exceptional functional group tolerance across structurally diverse substrates, including chiral molecules with complete stereochemical preservation. Notably, medium-sized macrolactones are efficiently constructed using this protocol. Being operationally simple and scalable, this platform exhibits practical versatility in late-stage functionalization of bioactive molecules, bioconjugation, and polymer chemistry, underscoring its broad synthetic utility.
{"title":"A TFPN-mediated acyl fluoride platform: efficient synthesis of esters, thioesters, and macrolactones from carboxylic acids with diverse nucleophiles†","authors":"Dou Zhang , Peng Shen , Yao Zhang , Qiuyi Zheng , Jiahui Zhang , Chunyu Han , Silin Xu , Jinhua Yang","doi":"10.1039/d5qo00651a","DOIUrl":"10.1039/d5qo00651a","url":null,"abstract":"<div><div>A TFPN (3,4,5,6-tetrafluorophthalonitrile)-mediated esterification strategy has been developed for the efficient synthesis of esters, thioesters, and macrolactones within remarkably short reaction times. Key to this approach is the utilization of <em>in situ</em>-generated acyl fluorides as transient intermediates, which circumvent stability limitations associated with conventional activated species. This method demonstrates exceptional functional group tolerance across structurally diverse substrates, including chiral molecules with complete stereochemical preservation. Notably, medium-sized macrolactones are efficiently constructed using this protocol. Being operationally simple and scalable, this platform exhibits practical versatility in late-stage functionalization of bioactive molecules, bioconjugation, and polymer chemistry, underscoring its broad synthetic utility.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 20","pages":"Pages 5414-5420"},"PeriodicalIF":0.0,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144184082","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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