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Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transferHighly Cited Paper

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dc.contributor.authorKleinmans, Roman-
dc.contributor.authorPinkert, Tobias-
dc.contributor.authorDutta, Subhabrata-
dc.contributor.authorPaulisch, Tiffany O.-
dc.contributor.authorHyeyun Keum-
dc.contributor.authorDaniliuc, Constantin G.-
dc.contributor.authorGlorius, Frank-
dc.date.accessioned2022-06-08T02:12:59Z-
dc.date.available2022-06-08T02:12:59Z-
dc.date.created2022-05-23-
dc.date.issued2022-05-
dc.identifier.issn0028-0836-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/11705-
dc.description.abstract© 2022, The Author(s), under exclusive licence to Springer Nature Limited.For more than one century, photochemical [2+2]-cycloadditions have been used by synthetic chemists to make cyclobutanes, four-membered carbon-based rings. In this reaction, typically two olefin subunits (two π-electrons per olefin) cyclize to form two new C–C σ-bonds. Although the development of photochemical [2+2]-cycloadditions has made enormous progress within the last century, research has been focused on such [2π+2π]-systems, in which two π-bonds are converted into two new σ-bonds1,2. Here we report an intermolecular [2+2]-photocycloaddition that uses bicyclo[1.1.0]butanes as 2σ-electron reactants3–7. This strain-release-driven [2π+2σ]-photocycloaddition reaction was realized by visible-light-mediated triplet energy transfer catalysis8,9. A simple, modular and diastereoselective synthesis of bicyclo[2.1.1]hexanes from heterocyclic olefin coupling partners, namely coumarins, flavones and indoles, is disclosed. Given the increasing importance of bicyclo[2.1.1]hexanes as bioisosteres—groups that convey similar biological properties to those they replace—in pharmaceutical research and considering their limited access10,11, there remains a need for new synthetic methodologies. Applying this strategy enabled us to extend the intermolecular [2+2]-photocycloadditions to σ-bonds and provides previously inaccessible structural motifs.-
dc.language영어-
dc.publisherNature Research-
dc.titleIntermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer-
dc.typeArticle-
dc.type.rimsART-
dc.identifier.wosid000793701100001-
dc.identifier.scopusid2-s2.0-85129265029-
dc.identifier.rimsid78192-
dc.contributor.affiliatedAuthorHyeyun Keum-
dc.identifier.doi10.1038/s41586-022-04636-x-
dc.identifier.bibliographicCitationNature, v.605, no.7910, pp.477 - 482-
dc.relation.isPartOfNature-
dc.citation.titleNature-
dc.citation.volume605-
dc.citation.number7910-
dc.citation.startPage477-
dc.citation.endPage482-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.description.journalClass1-
dc.description.isOpenAccessN-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalResearchAreaScience & Technology - Other Topics-
dc.relation.journalWebOfScienceCategoryMultidisciplinary Sciences-
dc.subject.keywordPlusSTRAIN-RELEASE-
dc.subject.keywordPlusCYCLOADDITION-
dc.subject.keywordPlusPHOTODIMERIZATION-
dc.subject.keywordAuthorSTRAIN-RELEASE-
dc.subject.keywordAuthorCYCLOADDITION-
dc.subject.keywordAuthorPHOTODIMERIZATION-
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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