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분자활성 촉매반응 연구단
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Switching Chemoselectivity Based on the Ring Size: How to Make Ring-Fused Indoles Using Transition-Metal-Mediated Cross-Coupling

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dc.contributor.authorKim, Jang-Yeop-
dc.contributor.authorWoojong Lee-
dc.contributor.authorKang, Hyung-Joon-
dc.contributor.authorJeon, Tae-Hong-
dc.contributor.authorMu-Hyun Baik-
dc.contributor.authorCho, Cheon-Gyu-
dc.date.accessioned2021-11-10T07:30:06Z-
dc.date.available2021-11-10T07:30:06Z-
dc.date.created2021-11-08-
dc.date.issued2021-10-15-
dc.identifier.issn2155-5435-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/10639-
dc.description.abstract© 2021 American Chemical SocietyPyrroloazocine indole alkaloids consisting of eight-membered azacycle fused to pyrrole and indole units exhibit intriguing pharmacological functions but still pose a synthetic challenge. Here, we report an alternative synthetic strategy for the pyrroloazocine indole core from two key steps: (i) regioselective Fischer indolization and (ii) transition-metal-mediated C-N cross-coupling reaction ofN-Boc aryl hydrazine with azacyclic vinyl triflate. In our investigation, Pd(0)- and Cu(I)-catalysts are found to display distinct and complementary selectivities for the ring size of cyclic vinyl triflates. For rings that are five- and six-membered, a Pd(0)-catalyst afforded the corresponding ene-hydrazines while completely ineffective for seven-membered or larger rings. A Cu(I)-catalyst exhibited the opposite selectivities. Computational studies reveal that their ring size dependency is due to the two bottlenecks of reductive elimination for Pd and oxidative addition for Cu along with bond strengths in products and reactants and degree of stage at transition states. These findings led us to establish a straightforward protocol for accessing a variety of ring-fused indoles highlighted with the formal synthesis of (−)-lundurine A.-
dc.language영어-
dc.publisherAmerican Chemical Society-
dc.titleSwitching Chemoselectivity Based on the Ring Size: How to Make Ring-Fused Indoles Using Transition-Metal-Mediated Cross-Coupling-
dc.typeArticle-
dc.type.rimsART-
dc.identifier.wosid000709692900038-
dc.identifier.scopusid2-s2.0-85117812736-
dc.identifier.rimsid76714-
dc.contributor.affiliatedAuthorWoojong Lee-
dc.contributor.affiliatedAuthorMu-Hyun Baik-
dc.identifier.doi10.1021/acscatal.1c03797-
dc.identifier.bibliographicCitationACS Catalysis, v.11, no.20, pp.12821 - 12832-
dc.relation.isPartOfACS Catalysis-
dc.citation.titleACS Catalysis-
dc.citation.volume11-
dc.citation.number20-
dc.citation.startPage12821-
dc.citation.endPage12832-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.description.journalClass1-
dc.description.isOpenAccessN-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalResearchAreaChemistry-
dc.relation.journalWebOfScienceCategoryChemistry, Physical-
dc.subject.keywordPlusEFFECTIVE CORE POTENTIALS-
dc.subject.keywordPlusCORRELATED MOLECULAR CALCULATIONS-
dc.subject.keywordPlusSOLVATION FREE-ENERGIES-
dc.subject.keywordPlusGAUSSIAN-BASIS SETS-
dc.subject.keywordPlusOXIDATIVE ADDITION-
dc.subject.keywordPlusPALLADIUM-
dc.subject.keywordPlusCOPPER-
dc.subject.keywordPlusARYL-
dc.subject.keywordPlusMECHANISM-
dc.subject.keywordPlusCONCISE-
dc.subject.keywordAuthorcopper-
dc.subject.keywordAuthorC−N cross-coupling-
dc.subject.keywordAuthordensity functional theory-
dc.subject.keywordAuthorintramolecular Fischer indolization-
dc.subject.keywordAuthorpalladium-
dc.subject.keywordAuthorpyrroloazocine indole alkaloid-
dc.subject.keywordAuthortransition-metal catalysis-
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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