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College of Natural Sciences(자연과학대학)Dept. of Chemistry(화학과)CH-Journal Papers(저널논문)

Boron-Catalyzed Silylative Reduction of Quinolines: Selective sp(3) C-Si Bond Formation

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dc.contributor.authorGandhamsetty, Narasimhuluko
dc.contributor.authorJoung, Seewonko
dc.contributor.authorPark, Sung-Wooko
dc.contributor.authorPark, Sehoonko
dc.contributor.authorChang, Suk-Bokko
dc.date.accessioned2015-11-20T09:10:01Z-
dc.date.available2015-11-20T09:10:01Z-
dc.date.created2015-01-05-
dc.date.created2015-01-05-
dc.date.issued2014-12-
dc.identifier.citationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.136, no.48, pp.16780 - 16783-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10203/201058-
dc.description.abstractA silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp(3)-Si bond exclusively beta to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp(3-)Si bond-forming step from the 1,4-adduct is facile.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.subjectFRUSTRATED LEWIS PAIRS-
dc.subjectB(C6F5)(3)-CATALYZED HYDROSILYLATION-
dc.subjectENOL ETHERS-
dc.subjectHYDROGENATION-
dc.subjectHYDROSILATION-
dc.subjectACTIVATION-
dc.subjectMECHANISM-
dc.subjectPYRIDINES-
dc.subjectTEMPERATURE-
dc.subjectOXIDATION-
dc.titleBoron-Catalyzed Silylative Reduction of Quinolines: Selective sp(3) C-Si Bond Formation-
dc.typeArticle-
dc.identifier.wosid000345883900021-
dc.identifier.scopusid2-s2.0-84915820391-
dc.type.rimsART-
dc.citation.volume136-
dc.citation.issue48-
dc.citation.beginningpage16780-
dc.citation.endingpage16783-
dc.citation.publicationnameJOURNAL OF THE AMERICAN CHEMICAL SOCIETY-
dc.identifier.doi10.1021/ja510674u-
dc.contributor.localauthorChang, Suk-Bok-
dc.contributor.nonIdAuthorGandhamsetty, Narasimhulu-
dc.contributor.nonIdAuthorPark, Sung-Woo-
dc.contributor.nonIdAuthorPark, Sehoon-
dc.type.journalArticleArticle-
dc.subject.keywordPlusFRUSTRATED LEWIS PAIRS-
dc.subject.keywordPlusB(C6F5)(3)-CATALYZED HYDROSILYLATION-
dc.subject.keywordPlusENOL ETHERS-
dc.subject.keywordPlusHYDROGENATION-
dc.subject.keywordPlusHYDROSILATION-
dc.subject.keywordPlusACTIVATION-
dc.subject.keywordPlusMECHANISM-
dc.subject.keywordPlusPYRIDINES-
dc.subject.keywordPlusTEMPERATURE-
dc.subject.keywordPlusOXIDATION-
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