Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline N-Oxides: Remote C-H Activation Using N-Oxide as a Stepping StoneHighly Cited Paper
DC Field | Value | Language |
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dc.contributor.author | Heejun Hwang | - |
dc.contributor.author | Jinwoo Kim | - |
dc.contributor.author | Jisu Jeong | - |
dc.contributor.author | Sukbok Chang | - |
dc.date.available | 2015-04-20T05:43:34Z | - |
dc.date.created | 2014-09-30 | - |
dc.date.issued | 2014-07 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/977 | - |
dc.description.abstract | Reported herein is the metal-catalyzed regioselective C-H functionalization of quinoline N-oxides at the 8-position: direct iodination and amidation were developed using rhodium and iridium catalytic systems, respectively. Mechanistic study of the amidation revealed that the unique regioselectivity is achieved through the smooth formation of N-oxide-chelated iridacycle and that an acid additive plays a key role in the rate-determining protodemetalation step. While this approach of remote C H activation using N-oxide as a directing group could readily be applied to a wide range of heterocyclic substrates under mild conditions with high functional group tolerance, an efficient synthesis of zinquin ester (a fluorescent zinc indicator) was demonstrated. | - |
dc.description.uri | 1 | - |
dc.language | 영어 | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline N-Oxides: Remote C-H Activation Using N-Oxide as a Stepping Stone | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 000339693900035 | - |
dc.identifier.scopusid | 2-s2.0-84905233935 | - |
dc.identifier.rimsid | 2154 | ko |
dc.date.tcdate | 2018-10-01 | - |
dc.contributor.affiliatedAuthor | Heejun Hwang | - |
dc.contributor.affiliatedAuthor | Jinwoo Kim | - |
dc.contributor.affiliatedAuthor | Jisu Jeong | - |
dc.contributor.affiliatedAuthor | Sukbok Chang | - |
dc.identifier.doi | 10.1021/ja5053768 | - |
dc.identifier.bibliographicCitation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.136, no.30, pp.10770 - 10776 | - |
dc.citation.title | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.volume | 136 | - |
dc.citation.number | 30 | - |
dc.citation.startPage | 10770 | - |
dc.citation.endPage | 10776 | - |
dc.date.scptcdate | 2018-10-01 | - |
dc.description.wostc | 171 | - |
dc.description.scptc | 174 | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.subject.keywordPlus | CARBON-HYDROGEN BONDS | - |
dc.subject.keywordPlus | DIRECT ARYLATION | - |
dc.subject.keywordPlus | OXIDATIVE CARBONYLATION | - |
dc.subject.keywordPlus | RHODIUM(I) CATALYST | - |
dc.subject.keywordPlus | RH(III) COMPLEXES | - |
dc.subject.keywordPlus | C(SP(3))-H BONDS | - |
dc.subject.keywordPlus | NITROGEN-SOURCE | - |
dc.subject.keywordPlus | PINCER COMPLEX | - |
dc.subject.keywordPlus | BENZOIC-ACIDS | - |
dc.subject.keywordPlus | PALLADIUM | - |