{"@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/1362825894251172736.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/adsc.200800750"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200800750"}},{"identifier":{"@type":"URI","@value":"https://advanced.onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200800750"}}],"dc:title":[{"@value":"Copper(II) Triflate as a Source of Triflic Acid: Effective, Green Catalysis of Hydroalkoxylation Reactions"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>The hydroalkoxylation of dicyclopentadiene (DCPD) and norbornene (NB) with 2‐hydroxyethyl methacrylate (HEMA) for the synthesis of industrially relevant monomers has been investigated with various metal‐based Lewis acids and strong Brønsted acids. In the absence of other additives, copper(II) triflate is the most efficient catalyst system. Kinetics, electron spin resonance (ESR), catalyst poisoning and cross experiments indicate that triflic acid (TfOH) is the true active catalyst in these reactions. This <jats:italic>in situ</jats:italic> generation of TfOH occurs <jats:italic>via</jats:italic> reduction of Cu(OTf)<jats:sub>2</jats:sub> by the olefin reagent (DCPD, NB). The copper ions present in the reaction mixture act as radical polymerization retardants, preventing polymerization of HEMA (which is observed with most other metal salts and strong Brønsted acids investigated), thus improving the selectivity and yield (up to 95%) for the desired products. These observations have led to the development of a highly effective green process, using bulk reagents (no solvent) and a cheap, metal‐free catalyst system, based on TfOH and a phenolic radical inhibitor (2,5‐di‐<jats:italic>tert</jats:italic>‐butylhydroxytoluene, BHT).</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380298343028476800","@type":"Researcher","foaf:name":[{"@value":"Mathieu J.‐L. Tschan"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825894251172736","@type":"Researcher","foaf:name":[{"@value":"Christophe M. Thomas"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825894251172610","@type":"Researcher","foaf:name":[{"@value":"Henri Strub"}]},{"@id":"https://cir.nii.ac.jp/crid/1380298343028476801","@type":"Researcher","foaf:name":[{"@value":"Jean‐François Carpentier"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"16154150"},{"@type":"EISSN","@value":"16154169"}],"prism:publicationName":[{"@value":"Advanced Synthesis & Catalysis"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"2009-10","prism:volume":"351","prism:number":"14-15","prism:startingPage":"2496","prism:endingPage":"2504"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200800750"},{"@id":"https://advanced.onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200800750"}],"createdAt":"2009-10-01","modifiedAt":"2025-10-06","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360285708569659520","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Iridium-catalyzed asymmetric cyclization of alkenoic acids leading to γ-lactones"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/adsc.200800750"},{"@type":"CROSSREF","@value":"10.1039/c5cc05393e_references_DOI_Wh487GjFKERXCexZAi8r3uqKD2z"}]}