{"@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/1360025430643102976.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/anie.202407150"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202407150"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Ligand‐Controlled Copper‐Catalyzed Halo‐Halodifluoromethylation of Alkenes and Alkynes Using Fluorinated Carboxylic Anhydrides"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>Polyhalogenated molecules are often found as bioactive compounds in nature and are used as synthetic building blocks. Fluoroalkyl compounds hold promise for the development of novel pharmaceuticals and agrochemicals, as the introduction of fluoroalkyl groups is known to improve lipophilicity, membrane permeability, and metabolic stability. Three‐component 1,2‐halo‐halodifluoromethylation reactions of alkenes are useful for their synthesis. However, general methods enabling the introduction of halodifluoromethyl (CF<jats:sub>2</jats:sub>X) and halogen (X’) groups in the desired combination of X and X’ are lacking. To address this gap, for the first time, we report a three‐component halo‐halodifluoromethylation of alkenes and alkynes using combinations of commercially available fluorinated carboxylic anhydrides ((CF<jats:sub>2</jats:sub>XCO)<jats:sub>2</jats:sub>O, X=Cl and Br) and alkali metal halides (X’=Cl and Br). In situ prepared fluorinated diacyl peroxides were identified as important intermediates, and the use of appropriate bipyridyl‐based ligands and a copper catalyst was essential for achieving high product selectivity. The synthetic utility of the polyhalogenated products was demonstrated by exploiting differences in the reactivities of their C−X and C−X’ bonds to achieve selective derivatization. Finally, the reaction mechanism and ligand effect were investigated using experimental and theoretical methods to provide important insights for the further development of catalytic reactions.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1030859912488943744","@type":"Researcher","foaf:name":[{"@value":"Subrata Mukherjee"}],"jpcoar:affiliationName":[{"@value":"Catalysis and Integrated Research Group RIKEN Center for Sustainable Resource Science  2-1 Hirosawa Wako Saitama 351-0198 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380025430643102848","@type":"Researcher","foaf:name":[{"@value":"Yuma Aoki"}],"jpcoar:affiliationName":[{"@value":"Catalysis and Integrated Research Group RIKEN Center for Sustainable Resource Science  2-1 Hirosawa Wako Saitama 351-0198 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380025430643102977","@type":"Researcher","foaf:name":[{"@value":"Shintaro Kawamura"}],"jpcoar:affiliationName":[{"@value":"Catalysis and Integrated Research Group RIKEN Center for Sustainable Resource Science  2-1 Hirosawa Wako Saitama 351-0198 Japan"},{"@value":"Synthetic Organic Chemistry Laboratory RIKEN Cluster for Pioneering Research  2-1 Hirosawa Wako Saitama 351-0198 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380025430643102849","@type":"Researcher","foaf:name":[{"@value":"Mikiko Sodeoka"}],"jpcoar:affiliationName":[{"@value":"Catalysis and Integrated Research Group RIKEN Center for Sustainable Resource Science  2-1 Hirosawa Wako Saitama 351-0198 Japan"},{"@value":"Synthetic Organic Chemistry Laboratory RIKEN Cluster for Pioneering Research  2-1 Hirosawa Wako Saitama 351-0198 Japan"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"14337851"},{"@type":"EISSN","@value":"15213773"}],"prism:publicationName":[{"@value":"Angewandte Chemie International Edition"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2024-09-02","prism:volume":"63","prism:number":"40"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202407150"}],"createdAt":"2024-07-09","modifiedAt":"2025-02-03","project":[{"@id":"https://cir.nii.ac.jp/crid/1040858906219286016","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"23KF0093"},{"@type":"JGN","@value":"JP23KF0093"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-23KF0093/"}],"notation":[{"@language":"ja","@value":"配位子-金属電荷移動遷移を鍵とする光鉄触媒の開発とフルオロアルキル化反応への応用"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360002214425440896","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Perfluoroalkylation of Unactivated Alkenes with Acid Anhydrides as the Perfluoroalkyl Source"}]},{"@id":"https://cir.nii.ac.jp/crid/1360004233131099904","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"<i>N</i>-Heterocycle-Forming Amino/Carboperfluoroalkylations of Aminoalkenes by Using Perfluoro Acid Anhydrides: Mechanistic Studies and Applications Directed Toward Perfluoroalkylated Compound Libraries"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011143552148864","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Metal-free alkene oxy- and amino-perfluoroalkylations <i>via</i> carbocation formation by using perfluoro acid anhydrides: unique reactivity between styrenes and perfluoro diacyl peroxides"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011143939113600","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Anodically Coupled Electrolysis for the Heterodifunctionalization of Alkenes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011145383704576","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Understanding organofluorine chemistry. 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