{"@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/1362825895205408896.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/chem.19970031219"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.19970031219"}},{"identifier":{"@type":"URI","@value":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.19970031219"}}],"dc:title":[{"@value":"Rapid Coupling of Methyl Iodide with Aryltributylstannanes Mediated by Palladium(0) Complexes: A General Protocol for the Synthesis of <sup>11</sup>CH<sub>3</sub>‐Labeled PET Tracers"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>The reaction of methyl iodide and (excess) aryltributylstannane to give a methylarene has been studied with the focus on the realization of rapid coupling for incorporation of short‐lived radionuclides into bioactive organic compounds. The coupling of methyl iodide with tributylphenylstannane (40 equiv) is accomplished in >90% yield within 5 min at 60°C with a tri‐<jats:italic>o</jats:italic>‐tolylphosphine‐bound, coordinatively unsaturated Pd<jats:sup>0</jats:sup> complex together with a Cu<jats:sup>I</jats:sup> salt and K<jats:sub>2</jats:sub>CO<jats:sub>3</jats:sub> in DMF. This protocol is applicable to a variety of homo‐ and heteroaromatic tin compounds, to give the corresponding methylated derivatives. The effects of the tri‐<jats:italic>o</jats:italic>‐tolylphosphine ligand, a Cu(I) salt, and DMF are discussed. This new protocol provides a firm chemical basis for the synthesis of <jats:sup>11</jats:sup>CH<jats:sub>3</jats:sub>‐incorporated PET tracers.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1382825895205408896","@type":"Researcher","foaf:name":[{"@value":"Masaaki Suzuki"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895205408768","@type":"Researcher","foaf:name":[{"@value":"Hisashi Doi"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895205408901","@type":"Researcher","foaf:name":[{"@value":"Margareta Björkman"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895205408899","@type":"Researcher","foaf:name":[{"@value":"Yvonne Andersson"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895205408897","@type":"Researcher","foaf:name":[{"@value":"Bengt Långström"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895205408898","@type":"Researcher","foaf:name":[{"@value":"Yasuyoshi Watanabe"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825895205408900","@type":"Researcher","foaf:name":[{"@value":"Ryoji Noyori"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"09476539"},{"@type":"EISSN","@value":"15213765"}],"prism:publicationName":[{"@value":"Chemistry – A European Journal"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"1997-12","prism:volume":"3","prism:number":"12","prism:startingPage":"2039","prism:endingPage":"2042"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.19970031219"},{"@id":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.19970031219"}],"createdAt":"2007-07-20","modifiedAt":"2025-10-12","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050845763735981184","@type":"Article","resourceType":"学術雑誌論文(journal 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<scp>PET</scp> Molecular Probes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285706992227456","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Blood–brain barrier permeability of ginkgolide: Comparison of the behavior of PET probes 7α-[18F]fluoro- and 10-O-p-[11C]methylbenzyl ginkgolide B in monkey and rat brains"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285708556545408","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Pd\n                    <sup>0</sup>\n                    -mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid esters: efficient method for incorporation of positron-emitting\n                    <sup>11</sup>\n                    C radionuclide into organic frameworks by coupling between two sp\n                    <sup>3</sup>\n                    -hybridized carbons"}]},{"@id":"https://cir.nii.ac.jp/crid/1360285714958373760","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"&lt;sup&gt;11&lt;/sup&gt;C-Labeling of the C(1)-C(10) Dihydroxy Acid Moiety for the Study on the Synthesis of Kulokekahilide-2 PET Tracer"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565169063036416","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Novel Rh(I)-Catalyzed Reaction of Arylzinc Compounds with Methyl Halides"}]},{"@id":"https://cir.nii.ac.jp/crid/1360567181970327808","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Synthesis of 11C-labeled retinoic acid, [11C]ATRA, via an alkenylboron precursor by Pd(0)-mediated rapid C-[11C]methylation"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001205311086208","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Pd0-Mediated Rapid C-[11C]Methylations and C-[18F]Fluoromethylations: Revolutionary New Methodologies for the Synthesis of Short-Lived PET Molecular Probes"},{"@value":"Pd[0]-mediated rapid C-〔11C〕methylations and C-〔18F〕fluoromethylations: revolutionary new methodologies for the synthesis of short-lived PET molecular probes"}]},{"@id":"https://cir.nii.ac.jp/crid/2051996266978160896","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Synthesis of a truncated analog of amphidinol 3 corresponding to the C21-C39/C52-C67 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