Intramolecular Aromatic Carbenoid Insertion of Biaryldiazoacetates for the Regioselective Synthesis of Fluorenes

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dc.contributor.authorKim, Jin-Hoko
dc.contributor.authorOk, You-Hwako
dc.contributor.authorPark, Sae-Humeko
dc.contributor.authorJung, You-Sungko
dc.contributor.authorChang, Suk-Bokko
dc.date.accessioned2013-03-11T00:20:07Z-
dc.date.available2013-03-11T00:20:07Z-
dc.date.created2012-02-06-
dc.date.created2012-02-06-
dc.date.issued2011-08-
dc.identifier.citationCHEMISTRY-AN ASIAN JOURNAL, v.6, pp.2039 - 2046-
dc.identifier.issn1861-4728-
dc.identifier.urihttp://hdl.handle.net/10203/97788-
dc.description.abstractThe rhodium- or copper-catalyzed intramolecular aromatic carbenoid insertion of biaryldiazoacetates offers a convenient route to fluorene carboxylates with high yields. Whereas, thermal conditions provided a mixture of two regioisomeric products when substituted biaryldiazoacetates were employed as substrates. The developed catalytic conditions displayed an excellent level of regioselectivity, presumably owing to steric effects. The insertion mechanism was assumed to be an electrophilic aromatic substitution, which was supported by preliminary mechanistic studies. A chloro-substituted fluorene derivative was efficiently synthesized and utilized as a base-sensitive protecting group of amines.-
dc.languageEnglish-
dc.publisherWILEY-BLACKWELL-
dc.subjectC-H INSERTION-
dc.subjectALPHA-DIAZOCARBONYL COMPOUNDS-
dc.subjectTERMINAL ALKYNES-
dc.subjectCYCLOPENTANE CONSTRUCTION-
dc.subjectINTERMOLECULAR REACTIONS-
dc.subjectCATALYZED DECOMPOSITION-
dc.subjectRHODIUM(II) ACETATE-
dc.subjectPYRROLE DERIVATIVES-
dc.subjectEFFICIENT SYNTHESIS-
dc.subjectPROTECTING GROUP-
dc.titleIntramolecular Aromatic Carbenoid Insertion of Biaryldiazoacetates for the Regioselective Synthesis of Fluorenes-
dc.typeArticle-
dc.identifier.wosid000294112200027-
dc.identifier.scopusid2-s2.0-79961051530-
dc.type.rimsART-
dc.citation.volume6-
dc.citation.beginningpage2039-
dc.citation.endingpage2046-
dc.citation.publicationnameCHEMISTRY-AN ASIAN JOURNAL-
dc.embargo.liftdate9999-12-31-
dc.embargo.terms9999-12-31-
dc.contributor.localauthorJung, You-Sung-
dc.contributor.localauthorChang, Suk-Bok-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorbiaryldiazoacetates-
dc.subject.keywordAuthorcatalysis-
dc.subject.keywordAuthorfluorenes-
dc.subject.keywordAuthorregioselectivity-
dc.subject.keywordAuthorrhodium-
dc.subject.keywordPlusC-H INSERTION-
dc.subject.keywordPlusALPHA-DIAZOCARBONYL COMPOUNDS-
dc.subject.keywordPlusTERMINAL ALKYNES-
dc.subject.keywordPlusCYCLOPENTANE CONSTRUCTION-
dc.subject.keywordPlusINTERMOLECULAR REACTIONS-
dc.subject.keywordPlusCATALYZED DECOMPOSITION-
dc.subject.keywordPlusRHODIUM(II) ACETATE-
dc.subject.keywordPlusPYRROLE DERIVATIVES-
dc.subject.keywordPlusEFFICIENT SYNTHESIS-
dc.subject.keywordPlusPROTECTING GROUP-
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