{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1050025960417035392.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"HDL","@value":"https://hdl.handle.net/2324/7347378"}},{"identifier":{"@type":"DOI","@value":"10.1021/acs.joc.5c00027"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.5c00027"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@language":"en","@value":"Hydrogen Bond-Controlled Site-Selective C(sp^3)–H Alkylation of Sulfonanilides"},{"@value":"Hydrogen Bond-Controlled Site-Selective C(sp<sup>3</sup>)–H Alkylation of Sulfonanilides"}],"dc:language":"en","description":[{"type":"Abstract","notation":[{"@language":"en","@value":"We successfully developed a decatungstate-catalyzed benzylic C(sp^3)–H alkylation of sulfonanilides by utilizing the hydrogen bond between the sulfonamide group of the substrates and decatungstate photocatalysts. Using this catalytic system, site-selective C(sp^3)–H alkylation was achieved at the benzylic position near the sulfonamide group."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1420845751139085056","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"30843148"},{"@type":"NRID","@value":"1000030843148"},{"@type":"ORCID","@value":"0000-0001-7588-3176"}],"foaf:name":[{"@language":"en","@value":"Sekine, Kohei"},{"@language":"ja","@value":"関根, 康平"},{"@language":"ja-Kana","@value":"セキネ, コウヘイ"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Institute for Materials Chemistry and Engineering, Kyushu University"},{"@language":"ja","@value":"九州大学先導物質化学研究所"},{"@language":"en","@value":"Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University"},{"@language":"ja","@value":"九州大学大学院総合理工学研究院総合理工学専攻"}]},{"@id":"https://cir.nii.ac.jp/crid/1070025960417035392","@type":"Researcher","foaf:name":[{"@language":"en","@value":"Jiang, Hui"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University"},{"@language":"ja","@value":"九州大学大学院総合理工学府総合理工学専攻"}]},{"@id":"https://cir.nii.ac.jp/crid/1420282801208347008","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"40372685"},{"@type":"NRID","@value":"1000040372685"},{"@type":"ORCID","@value":"0000-0002-8679-9487"},{"@type":"NRID","@value":"9000257729662"},{"@type":"NRID","@value":"9000014187099"},{"@type":"NRID","@value":"9000398791666"},{"@type":"NRID","@value":"9000257731449"},{"@type":"NRID","@value":"9000018771302"},{"@type":"NRID","@value":"9000001995934"},{"@type":"NRID","@value":"9000014224116"},{"@type":"NRID","@value":"9000259318916"},{"@type":"NRID","@value":"9000018233563"},{"@type":"NRID","@value":"9000019192831"},{"@type":"NRID","@value":"9000255703228"},{"@type":"NRID","@value":"9000257729404"},{"@type":"NRID","@value":"9000001115850"},{"@type":"NRID","@value":"9000257726754"},{"@type":"NRID","@value":"9000002107231"},{"@type":"NRID","@value":"9000412115595"},{"@type":"NRID","@value":"9000257727657"},{"@type":"NRID","@value":"9000000259957"},{"@type":"NRID","@value":"9000345433941"},{"@type":"NRID","@value":"9000337073723"},{"@type":"NRID","@value":"9000399837277"},{"@type":"NRID","@value":"9000257727981"},{"@type":"NRID","@value":"9000023629585"},{"@type":"NRID","@value":"9000002013794"},{"@type":"NRID","@value":"9000016386881"},{"@type":"NRID","@value":"9000257732851"},{"@type":"NRID","@value":"9000019212529"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0165519"}],"foaf:name":[{"@language":"en","@value":"Kuninobu, Yoichiro"},{"@language":"ja","@value":"國信, 洋一郎"},{"@language":"ja-Kana","@value":"クニノブ, ヨウイチロウ"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Institute for Materials Chemistry and Engineering, Kyushu University"},{"@language":"ja","@value":"九州大学先導物質化学研究所"},{"@language":"en","@value":"Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University"},{"@language":"ja","@value":"九州大学大学院総合理工学研究院総合理工学専攻"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00223263"},{"@type":"EISSN","@value":"15206904"},{"@type":"NCID","@value":"AA00704100"}],"prism:publicationName":[{"@language":"en","@value":"The Journal of Organic Chemistry"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"2025-02-27","prism:volume":"90","prism:number":"9","prism:startingPage":"3454","prism:endingPage":"3467"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","dc:rights":["This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © 2025 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.5c00027."],"url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.5c00027"}],"foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Alcohols","dc:title":"Alcohols"},{"@id":"https://cir.nii.ac.jp/all?q=Column%20chromatography","dc:title":"Column chromatography"},{"@id":"https://cir.nii.ac.jp/all?q=Gels","dc:title":"Gels"},{"@id":"https://cir.nii.ac.jp/all?q=Post-translational%20modification","dc:title":"Post-translational modification"},{"@id":"https://cir.nii.ac.jp/all?q=Silica","dc:title":"Silica"}],"dcterms:subject":[{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Alcohols"}]},{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Column chromatography"}]},{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Gels"}]},{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Post-translational modification"}]},{"subjectScheme":"Other","notation":[{"@language":"en","@value":"Silica"}]}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040018351905603968","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"24K01489"},{"@type":"JGN","@value":"JP24K01489"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-24K01489/"}],"notation":[{"@language":"ja","@value":"非共有結合性相互作用に着目した触媒の創製と高選択的C-H結合変換反応の開発"},{"@language":"en","@value":"Creation of Novel Catalysts and Development of Highly Selective C-H Transformations Focusing on Noncovalent Interactions"}]},{"@id":"https://cir.nii.ac.jp/crid/1040299749909351168","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"24K08413"},{"@type":"JGN","@value":"JP24K08413"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-24K08413/"}],"notation":[{"@language":"ja","@value":"芳香族炭素－窒素結合切断を利用した光駆動型二官能基化反応の開発"}]},{"@id":"https://cir.nii.ac.jp/crid/1040850857196775936","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"21H01941"},{"@type":"JGN","@value":"JP21H01941"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-21H01941/"}],"notation":[{"@language":"ja","@value":"炭素－水素結合変換反応における位置および立体選択性制御法の創出"},{"@language":"en","@value":"Creation of Regio- and Stereocontrol Methods of C-H Transformations"}]},{"@id":"https://cir.nii.ac.jp/crid/1040855511112362240","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"22H05370"},{"@type":"JGN","@value":"JP22H05370"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PUBLICLY-22H05370/"}],"notation":[{"@language":"ja","@value":"データサイエンスを利用する位置選択的かつエナンチオ選択的変換反応の開発"},{"@language":"en","@value":"Development of Regio- and Enantioselective Transformations Using Data Science"}]},{"@id":"https://cir.nii.ac.jp/crid/1860025960417035392","@type":"Project","notation":[{"@language":"en","@value":"Qdai-jump Research Program"},{"@language":"ja","@value":"ＱＲプログラム"}]},{"@id":"https://cir.nii.ac.jp/crid/1900022374800188928","@type":"Project","projectIdentifier":[{"@type":"JGN","@value":"JPMJSP2136"}],"notation":[{"@language":"ja","@value":"未来を拓く博士人材育成のためのオープンプラットフォーム型教育システムの構築"},{"@language":"en","@value":"Open Platform Fostering System for Ph.D. students who will open up the Future"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050585946603079552","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Boronyl-Group-Assisted Decatungstate-Catalyzed Benzylic C(sp^3)–H Alkylation"},{"@value":"Boronyl-Group-Assisted Decatungstate-Catalyzed Benzylic C(sp<sup>3</sup>)–H Alkylation"}]},{"@id":"https://cir.nii.ac.jp/crid/1360002216801222144","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"A meta-selective C–H borylation directed by a secondary interaction between ligand and substrate"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011144906642560","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Regioselective C–H Amidation of (Alkyl)arenes by Iron(II) Catalysis"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011146112473984","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation"}]},{"@id":"https://cir.nii.ac.jp/crid/1360016864734248192","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Control of Site-Selectivity in Hydrogen Atom Transfer by Electrostatic Interaction: Proximal-Selective C(sp<sup>3</sup>)–H Alkylation of 2-Methylanilinium Salts Using a Decatungstate Photocatalyst"}]},{"@id":"https://cir.nii.ac.jp/crid/1360016866458175744","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Arenethiolate as a Dual Function Catalyst for Photocatalytic Defluoroalkylation and Hydrodefluorination of Trifluoromethyls"}]},{"@id":"https://cir.nii.ac.jp/crid/1360020697619943808","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Non‐Covalent Interaction‐Controlled Site‐Selective C−H Transformations"}]},{"@id":"https://cir.nii.ac.jp/crid/1360020697620649984","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Decatungstate-Catalyzed C(sp<sup>3</sup>)–H Alkylation of a Val Residue Proximal to the N-Terminus Controlled by an Electrostatic Interaction"}]},{"@id":"https://cir.nii.ac.jp/crid/1360020700264502144","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C–H Bonds"}]},{"@id":"https://cir.nii.ac.jp/crid/1360025433692082432","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Nickel-(II)-Catalyzed <i>N</i>-Formylation and <i>N</i>-Acylation of Amines"}]},{"@id":"https://cir.nii.ac.jp/crid/1360283691592106496","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Site-Selective C–H Functionalization by Decatungstate Anion Photocatalysis: Synergistic Control by Polar and Steric Effects Expands the Reaction Scope"}]},{"@id":"https://cir.nii.ac.jp/crid/1360292620439977600","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Lewis Acid–Base Interaction‐Controlled <i>ortho</i>‐Selective C−H Borylation of Aryl Sulfides"}]},{"@id":"https://cir.nii.ac.jp/crid/1360294645881627520","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration"}]},{"@id":"https://cir.nii.ac.jp/crid/1360306913383353600","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds"}]},{"@id":"https://cir.nii.ac.jp/crid/1360306913487526144","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Synthesis of a Series of 2‐Aminodiarylsulfones by Brønsted Acid Mediated Regioselective Fries Type Rearrangement of\n                    <i>N</i>\n                    ‐Alkyl‐\n                    <i>N</i>\n                    ‐arylbenzenesulfonamides"}]},{"@id":"https://cir.nii.ac.jp/crid/1360306914216032256","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Recent advances of decatungstate photocatalyst in HAT process"}]},{"@id":"https://cir.nii.ac.jp/crid/1360306914250936320","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Recent advances of visible-light photocatalysis in the functionalization of organic compounds"}]},{"@id":"https://cir.nii.ac.jp/crid/1360572092722936832","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Recent progress of transition metal-catalysed regioselective C–H transformations based on noncovalent interactions"}]},{"@id":"https://cir.nii.ac.jp/crid/1360576123086737536","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions"}]},{"@id":"https://cir.nii.ac.jp/crid/1360580238889038208","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Semicarbazide: A Transient Directing Group for C(<i>sp</i><sup>3</sup>)−H Arylation of 2‐Methylbenzaldehydes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360588389222045952","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Hydroxy-directed fluorination of remote unactivated C(sp<sup>3</sup>)–H bonds: a new age of diastereoselective radical fluorination"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848658079598720","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Hydrogen Bond-Accelerated <i>meta</i>-Selective C–H Borylation of Aromatic Compounds and Expression of Functional Group and Substrate Specificities"}]},{"@id":"https://cir.nii.ac.jp/crid/1360855569288189568","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation"}]},{"@id":"https://cir.nii.ac.jp/crid/1360855570257491328","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Direct C−H Transformation via Iron Catalysis"}]},{"@id":"https://cir.nii.ac.jp/crid/1360857595602807168","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Catalytic enantioselective desymmetrizing functionalization of alkyl radicals via Cu(i)/CPA cooperative catalysis"}]},{"@id":"https://cir.nii.ac.jp/crid/1360861293066051968","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Meta Selective C–H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction"}]},{"@id":"https://cir.nii.ac.jp/crid/1360861294702712448","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"C–H activation"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137043683279104","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Remarkably Selective Iridium Catalysts for the Elaboration of Aromatic C-H Bonds"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137043811076992","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Early-Time Dynamics and Reactivity of Polyoxometalate Excited States. Identification of a Short-Lived LMCT Excited State and a Reactive Long-Lived Charge-Transfer Intermediate following Picosecond Flash Excitation of [W10O32]4- in Acetonitrile"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137043812497024","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"A Stoichiometric Aromatic CbH Borylation Catalyzed by Iridium(I)/2,2′-Bipyridine Complexes at Room Temperature"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137044685591424","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Functionalization of C(sp\n            <sup>3</sup>\n            )–H bonds using a transient directing group"}]},{"@id":"https://cir.nii.ac.jp/crid/1361699994657633920","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp<sup>3</sup>)–H Bonds"}]},{"@id":"https://cir.nii.ac.jp/crid/1361975842823746176","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds"}]},{"@id":"https://cir.nii.ac.jp/crid/1361981468863635840","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Urea-Mediated Protein Denaturation: A Consensus View"}]},{"@id":"https://cir.nii.ac.jp/crid/1362544418637806592","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Palladium-Catalyzed Fluorination of Carbon−Hydrogen Bonds"}]},{"@id":"https://cir.nii.ac.jp/crid/1363388844435803008","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Cooperativity in Noncovalent Interactions"}]},{"@id":"https://cir.nii.ac.jp/crid/1363670319104419456","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines"}]},{"@id":"https://cir.nii.ac.jp/crid/1363670319855040000","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate"}]},{"@id":"https://cir.nii.ac.jp/crid/1363951793479222144","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Decatungstate photocatalysis"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233269216451456","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)–Acetonitrile Complex"}]}],"dataSourceIdentifier":[{"@type":"IRDB","@value":"oai:irdb.nii.ac.jp:01211:0006722174"},{"@type":"CROSSREF","@value":"10.1021/acs.joc.5c00027"},{"@type":"KAKEN","@value":"PRODUCT-25654258"},{"@type":"KAKEN","@value":"PRODUCT-25756212"}]}