{"@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/1361699994757232768.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/anie.201709273"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201709273"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201709273"}}],"dc:title":[{"@value":"Thioamide‐Directed Cobalt(III)‐Catalyzed Selective Amidation of C(sp<sup>3</sup>)−H Bonds"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>A mild, oxidant‐free, and selective Cp*Co<jats:sup>III</jats:sup>‐catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp<jats:sup>3</jats:sup>)−H bond activation to generate the desired amidated products is reported. The method is efficient and allows for the C−H amidation of a wide range of functionalized thioamides with aryl‐, heteroaryl‐, and alkyl‐substituted dioxazolones under the Cp*Co<jats:sup>III</jats:sup>‐catalyzed conditions. The observed regioselectivity towards primary C(sp<jats:sup>3</jats:sup>)−H activation is supported by computational studies and the cyclometalation is proposed to proceed by means of an external carboxylate‐assisted concerted metalation/deprotonation mechanism. The reported method is a rare example of the use of a directing group other than the commonly used pyridine and quinolone classes for Cp*Co<jats:sup>III</jats:sup>‐catalyzed C(sp<jats:sup>3</jats:sup>)−H functionalization and the first to exploit thioamides.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1381699994757232772","@type":"Researcher","foaf:name":[{"@value":"Peng Wen Tan"}],"jpcoar:affiliationName":[{"@value":"Organic Chemistry Institute of Chemical and Engineering Sciences  8 Biomedical Grove, Neuros, #07-01 Singapore 138665 Singapore"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994757232771","@type":"Researcher","foaf:name":[{"@value":"Adrian M. Mak"}],"jpcoar:affiliationName":[{"@value":"Institute of High Performance Computing  1 Fusionopolis Way #16-16 Singapore 138632 Singapore"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994757232769","@type":"Researcher","foaf:name":[{"@value":"Michael B. Sullivan"}],"jpcoar:affiliationName":[{"@value":"Institute of High Performance Computing  1 Fusionopolis Way #16-16 Singapore 138632 Singapore"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994757232770","@type":"Researcher","foaf:name":[{"@value":"Darren J. Dixon"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry Chemistry Research Laboratory University of Oxford  12 Mansfield Road Oxford UK"}]},{"@id":"https://cir.nii.ac.jp/crid/1381699994757232768","@type":"Researcher","foaf:name":[{"@value":"Jayasree Seayad"}],"jpcoar:affiliationName":[{"@value":"Organic Chemistry Institute of Chemical and Engineering Sciences  8 Biomedical Grove, Neuros, #07-01 Singapore 138665 Singapore"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"14337851"},{"@type":"EISSN","@value":"15213773"}],"prism:publicationName":[{"@value":"Angewandte Chemie International Edition"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2017-11-30","prism:volume":"56","prism:number":"52","prism:startingPage":"16550","prism:endingPage":"16554"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201709273"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201709273"}],"createdAt":"2017-10-28","modifiedAt":"2023-09-18","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050587981426805632","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Native Amide-Directed C(sp3)−H Amidation Enabled by Electron-Deficient RhIII Catalyst and Electron-Deficient 2-Pyridone Ligand"},{"@value":"Native Amide‐Directed C(sp<sup>3</sup>)−H Amidation Enabled by Electron‐Deficient Rh<sup>III</sup> Catalyst and Electron‐Deficient 2‐Pyridone Ligand"}]},{"@id":"https://cir.nii.ac.jp/crid/1050869456405130496","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Chiral 2-Aryl Ferrocene Carboxylic Acids for the Catalytic Asymmetric C(sp(3))-H Activation of Thioamides"},{"@value":"Chiral 2-Aryl Ferrocene Carboxylic Acids for the Catalytic Asymmetric C(sp<sup>3</sup>)–H Activation of Thioamides"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285704973260160","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Recent Progress on Cyclic Nitrenoid Precursors in Transition‐Metal‐Catalyzed Nitrene‐Transfer Reactions"}]},{"@id":"https://cir.nii.ac.jp/crid/1360286989542067712","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Diverse Approaches for Enantioselective C−H Functionalization Reactions Using Group 9 Cp<sup>x</sup>M<sup>III</sup> Catalysts"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567179848186496","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Cobalt‐Catalyzed C(sp<sup>3</sup>)−H Functionalization Reactions"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567179949643648","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Weinreb Amide Directed Versatile C−H Bond Functionalization under (η<sup>5</sup>‐Pentamethylcyclopentadienyl)cobalt(III) Catalysis"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567189714729344","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"One-Step Synthesis of 4H-3,1-Benzoxazin-4-ones from Weinreb Amides and 1,4,2-Dioxazol-5-ones via Cobalt-Catalyzed C–H Bond Activation"}]},{"@id":"https://cir.nii.ac.jp/crid/1360576118771927296","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Chiral Carboxylic Acid Assisted Enantioselective C–H Activation with Achiral Cp<sup>x</sup>M<sup>III</sup> (M = Co, Rh, Ir) Catalysts"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848654856717440","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Enantioselective C(sp<sup>3</sup>)–H Amidation of Thioamides Catalyzed by a Cobalt<sup>III</sup>/Chiral Carboxylic Acid Hybrid System"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848658079465728","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Divergent Catalytic Approach from Cyclic Oxime Esters to Nitrogen-Containing Heterocycles with Group 9 Metal Catalysts"}]},{"@id":"https://cir.nii.ac.jp/crid/2050307417131935488","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Enantioselective C-H functionalization using high-valent group 9 metal catalysts"}]},{"@id":"https://cir.nii.ac.jp/crid/2051433317038773632","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Synthesis of an organometallic alkyl-Co(Ⅲ) complex with amidoquinoline directing groups via C(sp3)-H activation and its UV-vis/NMR spectroscopic, crystallographic, DFT, and electrochemical studies"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/anie.201709273"},{"@type":"CROSSREF","@value":"10.1021/acs.organomet.9b00407_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20210425_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1002/anie.202213659_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1002/chem.201803716_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1002/chem.201905417_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1021/acscatal.8b01646_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1002/ajoc.201800195_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1002/chem.201801750_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.3987/com-18-s(f)48_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1021/acscatal.1c01351_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20220168_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"},{"@type":"CROSSREF","@value":"10.1002/anie.201812215_references_DOI_WxewBe0V0vldQiIYbxDhI7N6tIr"}]}