{"@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/1360574096045462016.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/cjoc.201600029"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcjoc.201600029"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/cjoc.201600029"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/am-pdf/10.1002/cjoc.201600029"}},{"identifier":{"@type":"DOI","@value":"10.1002/chin.201639043"}}],"dc:title":[{"@value":"Activation of Trifluoromethylthio Moiety by Appending Iodonium Ylide under Copper Catalysis for Electrophilic Trifluoromethylation Reaction"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>A novel iodonium‐ylide compound <jats:bold>2 </jats:bold>that appends atrifluoromethylthio (SCF<jats:sub>3</jats:sub>) group is disclosed as a new, shelf‐stable electrophilic trifluoromethylation reagent. Unlike known shelf‐stable electrophilic trifluoromethylation reagents, <jats:bold>2</jats:bold> has a stable SCF<jats:sub>3</jats:sub> group which is activated by appending iodonium ylide under copper catalysis via sulfonium ylide to generate a cationic trifluoromethyl (CF<jats:sub>3</jats:sub>) species. Reagent <jats:bold>2</jats:bold> was found to be an efficient electrophilic trifluoromethylation reagent for a wide range of silyl enol ethers <jats:bold>3</jats:bold> under copper catalysis. Cyclic and acyclic <jats:italic>α</jats:italic>‐trifluoromethyl ketones <jats:bold>4</jats:bold> were obtained by reagent <jats:bold>2</jats:bold> in moderate to good yields. On the other hand, a difluoromethylthio analogue <jats:bold>5</jats:bold> did not affect intermolecular transfer difluoromethylation to substrates. Instead, intramolecular 1,4‐migration proceeded similar to the Stevens rearrangement to provide <jats:bold>6</jats:bold> in 21% yield, independent of the presence of nucleophiles <jats:bold>3</jats:bold>.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380574096045462144","@type":"Researcher","foaf:name":[{"@value":"Ibrayim Saidalimu"}]},{"@id":"https://cir.nii.ac.jp/crid/1380574096045462017","@type":"Researcher","foaf:name":[{"@value":"Shugo Suzuki"}]},{"@id":"https://cir.nii.ac.jp/crid/1380574096045462018","@type":"Researcher","foaf:name":[{"@value":"Etsuko Tokunaga"}]},{"@id":"https://cir.nii.ac.jp/crid/1380574096045462016","@type":"Researcher","foaf:name":[{"@value":"Norio Shibata"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"1001604X"},{"@type":"EISSN","@value":"16147065"}],"prism:publicationName":[{"@value":"Chinese Journal of Chemistry"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2016-03-08","prism:volume":"34","prism:number":"5","prism:startingPage":"485","prism:endingPage":"489"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#am","http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcjoc.201600029"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/cjoc.201600029"},{"@id":"https://onlinelibrary.wiley.com/doi/am-pdf/10.1002/cjoc.201600029"}],"createdAt":"2016-03-08","modifiedAt":"2023-09-10","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1390001204142494208","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Development of Shelf-Stable Reagents for Fluoro-Functionalization Reactions"},{"@value":"Award Accounts : The Chemical Society of Japan Award for Creative Work for 2014 : Development of Shelf-Stable Reagents for Fluoro-Functionalization Reactions"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/cjoc.201600029"},{"@type":"OPENAIRE","@value":"doi_dedup___::2b949f2070ce3b57a4e52cc68b94b4f7"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20160223_references_DOI_GhDkJmYp9munEeOKJXRu6OOJj19"}]}