Unusual 1,2-Aryl Migration and Depalladation of Alkylpalladium Intermediates Containing a syn-beta-Hydrogen Atom
DC Field | Value | Language |
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dc.contributor.author | Youn, So Won | - |
dc.contributor.author | Lee, So Ra | - |
dc.contributor.author | Kim, Yun Ah | - |
dc.contributor.author | Kang, Da Young | - |
dc.contributor.author | Jang, Min Jung | - |
dc.date.accessioned | 2022-07-15T04:21:49Z | - |
dc.date.available | 2022-07-15T04:21:49Z | - |
dc.date.created | 2021-05-12 | - |
dc.date.issued | 2016-11 | - |
dc.identifier.issn | 2365-6549 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/153645 | - |
dc.description.abstract | In general, alkylpalladium intermediates containing a syn beta-hydrogen atom are expected to undergo beta-hydride elimination preferentially. However, this study unveils a new mechanistic mode in a Pd(II)-catalyzed transformation, which leads to a series of both C-N/C-C bond forming and C-C bond forming/cleavage events. It has been demonstrated that a Pd(II)catalyzed oxidative cyclization of stilbenes bearing a pendent nucleophile such as 2-alkenylanilines and 2-alkenylphenyl 1,3-diketones operates through an uncommon Pd-C bond cleavage assisted by a neighboring aryl group and CuCl2-assisted transient Pd oxidation, rather than generally preferred beta-hydride elimination in alkylpalladium intermediates containing a syn beta-hydrogen atom. As a result, 1,2-aryl migration occurs to lead to the unexpected formation of a variety of 3-substituted indoles and 4-aryl-1-naphthols. In addition, selective migration of an aryl group could be achieved from beta,beta-disubstituted alkene substrates through alkylpalladium intermediates deprived of syn beta-hydrogen atom. | - |
dc.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.title | Unusual 1,2-Aryl Migration and Depalladation of Alkylpalladium Intermediates Containing a syn-beta-Hydrogen Atom | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Youn, So Won | - |
dc.identifier.doi | 10.1002/slct.201601382 | - |
dc.identifier.scopusid | 2-s2.0-85000590145 | - |
dc.identifier.wosid | 000395427600025 | - |
dc.identifier.bibliographicCitation | CHEMISTRYSELECT, v.1, no.18, pp.5749 - 5757 | - |
dc.relation.isPartOf | CHEMISTRYSELECT | - |
dc.citation.title | CHEMISTRYSELECT | - |
dc.citation.volume | 1 | - |
dc.citation.number | 18 | - |
dc.citation.startPage | 5749 | - |
dc.citation.endPage | 5757 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.isOpenAccess | N | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | C-H AMINATION | - |
dc.subject.keywordPlus | ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS | - |
dc.subject.keywordPlus | PALLADIUM-CATALYZED REACTIONS | - |
dc.subject.keywordPlus | REDUCTIVE ELIMINATION | - |
dc.subject.keywordPlus | CONJUGATE ADDITION | - |
dc.subject.keywordPlus | BOND FORMATION | - |
dc.subject.keywordPlus | INTRAMOLECULAR AMINOPALLADATION | - |
dc.subject.keywordPlus | REGIOCONTROLLED SYNTHESIS | - |
dc.subject.keywordPlus | 4-SUBSTITUTED INDOLES | - |
dc.subject.keywordPlus | HYDRIDE ELIMINATION | - |
dc.subject.keywordAuthor | 1,2-aryl migration | - |
dc.subject.keywordAuthor | cyclization | - |
dc.subject.keywordAuthor | palladium | - |
dc.subject.keywordAuthor | rearrangement | - |
dc.identifier.url | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.201601382 | - |
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