The Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes

Cited 1 time in webofscience Cited 0 time in scopus
  • Hit : 96
  • Download : 0
DC FieldValueLanguage
dc.contributor.authorKim, Hong Kiko
dc.contributor.authorMane, Manoj, Vko
dc.contributor.authorMontgomery, Johnko
dc.contributor.authorBaik, Mu-Hyunko
dc.date.accessioned2019-09-10T05:20:09Z-
dc.date.available2019-09-10T05:20:09Z-
dc.date.created2019-09-09-
dc.date.created2019-09-09-
dc.date.issued2019-07-
dc.identifier.citationCHEMISTRY-A EUROPEAN JOURNAL, v.25, no.40, pp.9456 - 9463-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10203/267450-
dc.description.abstractA highly selective copper-catalyzed trifunctionalization of allenes has been established based on diborylation/cyanation with bis(pinacolato)diboron (B(2)pin(2)) and N-cyano-N-phenyl-p-toluenesulfonamide (NCTS). The Cu-catalyzed trifunctionalization of terminal allenes is composed of three catalytic reactions (first borocupration, electrophilic cyanation, and second borocupration) that provide a densely functionalized product with regio-, chemo- and diastereoselectivity. Allene substrates have multiple reaction-sites, and the selectivities are determined by the suitable interactions (e.g., electronic and steric demands) between the catalyst and substrates. We employed DFT calculations to understand the cascade copper-catalyzed trifunctionalization of terminal allenes, providing densely-functionalized organic molecules with outstanding regio-, chemo- and diastereoselectivity in high yields. The selectivity challenges presented by cumulated pi-systems are addressed by systematic computational studies; these give insight to the catalytic multiple-functionalization strategies and explain the high selectivities that we see for these reactions.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleThe Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes-
dc.typeArticle-
dc.identifier.wosid000482329000020-
dc.identifier.scopusid2-s2.0-85065094868-
dc.type.rimsART-
dc.citation.volume25-
dc.citation.issue40-
dc.citation.beginningpage9456-
dc.citation.endingpage9463-
dc.citation.publicationnameCHEMISTRY-A EUROPEAN JOURNAL-
dc.identifier.doi10.1002/chem.201900673-
dc.contributor.localauthorBaik, Mu-Hyun-
dc.contributor.nonIdAuthorMane, Manoj, V-
dc.contributor.nonIdAuthorMontgomery, John-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle; Proceedings Paper-
dc.subject.keywordAuthorborylation-
dc.subject.keywordAuthorcopper catalysis-
dc.subject.keywordAuthorcyanation-
dc.subject.keywordAuthordensity functional theory-
dc.subject.keywordAuthorselectivities-
dc.subject.keywordAuthortrifunctionalization-
dc.subject.keywordPlusSOLVATION FREE-ENERGIES-
dc.subject.keywordPlusC-H CYANATION-
dc.subject.keywordPlusMOLECULAR CALCULATIONS-
dc.subject.keywordPlusASYMMETRIC-SYNTHESIS-
dc.subject.keywordPlusHYDROBORATION-
dc.subject.keywordPlusALKENES-
dc.subject.keywordPlus1,2,3-TRIFUNCTIONALIZATION-
dc.subject.keywordPlusADDITIONS-
dc.subject.keywordPlusMODEL-
dc.subject.keywordPlusBORON-
Appears in Collection
CH-Journal Papers(저널논문)
Files in This Item
There are no files associated with this item.
This item is cited by other documents in WoS
⊙ Detail Information in WoSⓡ Click to see webofscience_button
⊙ Cited 1 items in WoS Click to see citing articles in records_button

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0