Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides
DC Field | Value | Language |
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dc.contributor.author | Yonghoon Moon | - |
dc.contributor.author | Wooseok Lee | - |
dc.contributor.author | Sungwoo Hong | - |
dc.date.accessioned | 2020-12-22T02:57:58Z | - |
dc.date.accessioned | 2020-12-22T02:57:58Z | - |
dc.date.available | 2020-12-22T02:57:58Z | - |
dc.date.available | 2020-12-22T02:57:58Z | - |
dc.date.created | 2020-09-09 | - |
dc.date.issued | 2020-07 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/7777 | - |
dc.description.abstract | © 2020 American Chemical Society.By utilizing an underexplored reactivity mode of N-aminopyridinium ylides, we developed the visible-light-induced ortho-selective aminopyridylation of alkenes via radical-mediated 1,3-dipolar cycloaddition. The photocatalyzed single-electron oxidation of N-aminopyridinium ylides generates the corresponding radical cations that enable previously inaccessible 1,3-cycloaddition with a broader range of alkene substrates. The resulting cycloaddition adducts rapidly undergo subsequent homolytic cleavage of the N-N bond, conferring a substantial thermodynamic driving force to yield various β-aminoethylpyridines. Remarkably, amino and pyridyl groups can be installed into both activated and unactivated alkenes with modular control of ortho-selectivity and 1,2-syn-diastereoselectivity under metal-free and mild conditions. Combined experimental and computational studies are conducted to clarify the detailed reaction mechanism and the origins of site selectivity and diastereoselectivity | - |
dc.description.uri | 1 | - |
dc.language | 영어 | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | C-H FUNCTIONALIZATION | - |
dc.subject | PHOTOREDOX CATALYSIS | - |
dc.subject | CYCLOADDITION REACTIONS | - |
dc.subject | UNACTIVATED ALKENES | - |
dc.subject | HYDROAMINATION | - |
dc.subject | ALKYLATION | - |
dc.subject | HETEROARYLATION | - |
dc.subject | PYRIDYLATION | - |
dc.subject | ALDEHYDES | - |
dc.subject | REAGENTS | - |
dc.title | Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 000551495700058 | - |
dc.identifier.scopusid | 2-s2.0-85088120235 | - |
dc.identifier.rimsid | 72764 | - |
dc.contributor.affiliatedAuthor | Yonghoon Moon | - |
dc.contributor.affiliatedAuthor | Wooseok Lee | - |
dc.contributor.affiliatedAuthor | Sungwoo Hong | - |
dc.identifier.doi | 10.1021/jacs.0c05025 | - |
dc.identifier.bibliographicCitation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.28, pp.12420 - 12429 | - |
dc.citation.title | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.volume | 142 | - |
dc.citation.number | 28 | - |
dc.citation.startPage | 12420 | - |
dc.citation.endPage | 12429 | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.subject.keywordPlus | C-H FUNCTIONALIZATION | - |
dc.subject.keywordPlus | PHOTOREDOX CATALYSIS | - |
dc.subject.keywordPlus | CYCLOADDITION REACTIONS | - |
dc.subject.keywordPlus | UNACTIVATED ALKENES | - |
dc.subject.keywordPlus | HYDROAMINATION | - |
dc.subject.keywordPlus | ALKYLATION | - |
dc.subject.keywordPlus | HETEROARYLATION | - |
dc.subject.keywordPlus | PYRIDYLATION | - |
dc.subject.keywordPlus | ALDEHYDES | - |
dc.subject.keywordPlus | REAGENTS | - |