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Hydrogen-Bond-Assisted Controlled C–H Functionalization via Adaptive Recognition of a Purine Directing Group : Hydrogen-Bond-Assisted Controlled C-H Functionalization via Adaptive Recognition of a Purine Directing Group
DC Field | Value | Language |
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dc.contributor.author | Kim, Hyun Jin | - |
dc.contributor.author | Ajitha, Manjaly J. | - |
dc.contributor.author | Lee, Yongjae | - |
dc.contributor.author | Ryu, Jaeyune | - |
dc.contributor.author | Kim, Jin | - |
dc.contributor.author | Lee, Yunho | - |
dc.contributor.author | Jung, Yousung | - |
dc.contributor.author | Chang, Sukhok | - |
dc.date.accessioned | 2023-05-03T05:46:59Z | - |
dc.date.available | 2023-05-03T05:46:59Z | - |
dc.date.created | 2023-05-01 | - |
dc.date.created | 2023-05-01 | - |
dc.date.created | 2023-05-01 | - |
dc.date.issued | 2014-01 | - |
dc.identifier.citation | Journal of the American Chemical Society, Vol.136 No.3, pp.1132-1140 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://hdl.handle.net/10371/191821 | - |
dc.description.abstract | We have developed the Rh-catalyzed selective C-H functionalization of 6-arylpurines, in which the purine moiety directs the C-H bond activation of the aryl pendant. While the first C-H amination proceeds via the N1-chelation assistance, the subsequent second C-H bond activation takes advantage of an intramolecular hydrogen-bonding interaction between the initially formed amino group and one nitrogen atom, either N1 or N7, of the purinyl part. Isolation of a rhodacycle intermediate and the substrate variation studies suggest that N1 is the main active site for the C-H functionalization of both the first and second amination in 6-arylpurines, while N7 plays an essential role in controlling the degree of functionalization serving as an intramolecular hydrogen-bonding site in the second amination process. This pseudo-Curtin-Hammett situation was supported by density functional calculations, which suggest that the intramolecular hydrogen-bonding capability helps second amination by reducing the steric repulsion between the first installed ArNH and the directing group. | - |
dc.language | 영어 | - |
dc.publisher | American Chemical Society | - |
dc.title | Hydrogen-Bond-Assisted Controlled C–H Functionalization via Adaptive Recognition of a Purine Directing Group | - |
dc.title.alternative | Hydrogen-Bond-Assisted Controlled C-H Functionalization via Adaptive Recognition of a Purine Directing Group | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/ja4118472 | - |
dc.citation.journaltitle | Journal of the American Chemical Society | - |
dc.identifier.wosid | 000330202300050 | - |
dc.identifier.scopusid | 2-s2.0-84892995915 | - |
dc.citation.endpage | 1140 | - |
dc.citation.number | 3 | - |
dc.citation.startpage | 1132 | - |
dc.citation.volume | 136 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Ryu, Jaeyune | - |
dc.contributor.affiliatedAuthor | Lee, Yunho | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | ASYMMETRIC MICHAEL ADDITION | - |
dc.subject.keywordPlus | MUKAIYAMA ALDOL REACTIONS | - |
dc.subject.keywordPlus | CATALYZED ORTHO-ARYLATION | - |
dc.subject.keywordPlus | CROSS-COUPLING REACTIONS | - |
dc.subject.keywordPlus | DIELS-ALDER REACTIONS | - |
dc.subject.keywordPlus | CARBON-CARBON BONDS | - |
dc.subject.keywordPlus | SIMPLE ARENES | - |
dc.subject.keywordPlus | 6-ARYLPURINE NUCLEOSIDES | - |
dc.subject.keywordPlus | CYTOSTATIC ACTIVITY | - |
dc.subject.keywordPlus | ARYL AZIDES | - |
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