Remote C−H Pyridylation of Hydroxamates through Direct Photoexcitation of O-Aryl Oxime Pyridinium Intermediates
DC Field | Value | Language |
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dc.contributor.author | Byeongseok Kweon | - |
dc.contributor.author | Changha Kim | - |
dc.contributor.author | Seonyul Kim | - |
dc.contributor.author | Sungwoo Hong | - |
dc.date.accessioned | 2021-12-16T00:30:09Z | - |
dc.date.available | 2021-12-16T00:30:09Z | - |
dc.date.created | 2021-12-15 | - |
dc.date.issued | 2021-12-13 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/10844 | - |
dc.description.abstract | © 2021 Wiley-VCH GmbHHerein, we report an efficient strategy for the remote C−H pyridylation of hydroxamates with excellent ortho-selectivity by designing a new class of photon-absorbing O-aryl oxime pyridinium salts generated in situ from the corresponding pyridines and hydroxamates. When irradiated by visible light, the photoexcitation of oxime pyridinium intermediates generates iminyl radicals via the photolytic N−O bond cleavage, which does not require an external photocatalyst. The efficiency of light absorption and N−O bond cleavage of the oxime pyridinium salts can be modulated through the electronic effect of substitution on the O-aryl ring. The resultant iminyl radicals enable the installation of pyridyl rings at the γ-CN position, which yields synthetically valuable C2-substituted pyridyl derivatives. This novel synthetic approach provides significant advantages in terms of both efficiency and simplicity and exhibits broad functional group tolerance in complex settings under mild and metal-free conditions. | - |
dc.language | 영어 | - |
dc.publisher | John Wiley and Sons Inc | - |
dc.title | Remote C−H Pyridylation of Hydroxamates through Direct Photoexcitation of O-Aryl Oxime Pyridinium Intermediates | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 000718391300001 | - |
dc.identifier.scopusid | 2-s2.0-85119377095 | - |
dc.identifier.rimsid | 76825 | - |
dc.contributor.affiliatedAuthor | Byeongseok Kweon | - |
dc.contributor.affiliatedAuthor | Changha Kim | - |
dc.contributor.affiliatedAuthor | Seonyul Kim | - |
dc.contributor.affiliatedAuthor | Sungwoo Hong | - |
dc.identifier.doi | 10.1002/anie.202112364 | - |
dc.identifier.bibliographicCitation | Angewandte Chemie - International Edition, v.60, no.51, pp.26813 - 26821 | - |
dc.relation.isPartOf | Angewandte Chemie - International Edition | - |
dc.citation.title | Angewandte Chemie - International Edition | - |
dc.citation.volume | 60 | - |
dc.citation.number | 51 | - |
dc.citation.startPage | 26813 | - |
dc.citation.endPage | 26821 | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
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 | NITROGEN-CENTERED RADICALS | - |
dc.subject.keywordPlus | LIGHT-MEDIATED GENERATION | - |
dc.subject.keywordPlus | FUNCTIONALIZATION | - |
dc.subject.keywordPlus | ALKYLATION | - |
dc.subject.keywordPlus | HETEROCYCLES | - |
dc.subject.keywordPlus | ARYLATION | - |
dc.subject.keywordPlus | ALKENES | - |
dc.subject.keywordPlus | HETEROARYLATION | - |
dc.subject.keywordPlus | PHENANTHRIDINES | - |
dc.subject.keywordPlus | PRECURSORS | - |
dc.subject.keywordAuthor | heterocycles | - |
dc.subject.keywordAuthor | iminyl radicals | - |
dc.subject.keywordAuthor | oximes | - |
dc.subject.keywordAuthor | photochemistry | - |
dc.subject.keywordAuthor | reaction mechanisms | - |