Site-Selective 1,1-Difunctionalization of Unactivated Alkenes Enabled by Cationic Palladium Catalysis

Cited 9 time in webofscience Cited 0 time in scopus
  • Hit : 110
  • Download : 0
DC FieldValueLanguage
dc.contributor.authorJeon, Jinwonko
dc.contributor.authorRyu, Hoko
dc.contributor.authorLee, Changseokko
dc.contributor.authorCho, Dasolko
dc.contributor.authorBaik, Mu-Hyunko
dc.contributor.authorHong, Sungwooko
dc.date.accessioned2019-07-22T05:10:06Z-
dc.date.available2019-07-22T05:10:06Z-
dc.date.created2019-07-02-
dc.date.created2019-07-02-
dc.date.issued2019-06-
dc.identifier.citationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.25, pp.10048 - 10059-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10203/263682-
dc.description.abstractA palladium(II)-catalyzed 1,1-difunctionalization of unactivated terminal and internal alkenes via addition of two nucleophiles was developed using a cationic palladium(II) complex. The palladacycle generated in situ as a result of a regioselective addition of a nucleophile to the alkene can readily undergo regioselective beta-hydride elimination and migratory insertion with a cationic palladium catalyst. The resulting eta(3)-pi-allyl palladium(II) complex is the key intermediate that reacts with a second nucleophile to furnish the desired 1,1-difunctionalization of the alkene. Under the optimized reaction conditions, a wide range of indoles and anilines add to alkene units of 3-butenoic or 4-pentenoic acid derivatives to afford the synthetically useful gamma,gamma- or delta,delta-difunctionalized products with excellent regiocontrol. Furthermore, by employing internal hydroxyl or acid groups and external carbon nucleophiles, this transformation enables unsymmetric 1,1-difunctionalization to forge challenging and important oxo quaternary carbon centers. Combining experiments and DFT calculations on the mechanism of the reaction is investigated in detail.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.titleSite-Selective 1,1-Difunctionalization of Unactivated Alkenes Enabled by Cationic Palladium Catalysis-
dc.typeArticle-
dc.identifier.wosid000473251500041-
dc.identifier.scopusid2-s2.0-85067998374-
dc.type.rimsART-
dc.citation.volume141-
dc.citation.issue25-
dc.citation.beginningpage10048-
dc.citation.endingpage10059-
dc.citation.publicationnameJOURNAL OF THE AMERICAN CHEMICAL SOCIETY-
dc.identifier.doi10.1021/jacs.9b04142-
dc.contributor.localauthorBaik, Mu-Hyun-
dc.contributor.localauthorHong, Sungwoo-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordPlusC-H ACTIVATION-
dc.subject.keywordPlusORGANOBORONIC ACIDS-
dc.subject.keywordPlusINTERMOLECULAR AMINOACETOXYLATION-
dc.subject.keywordPlusCYCLIZATION REACTION-
dc.subject.keywordPlusC(SP(3))-H BONDS-
dc.subject.keywordPlusTERMINAL ALKENES-
dc.subject.keywordPlusDIFUNCTIONALIZATION-
dc.subject.keywordPlusCONSTRUCTION-
dc.subject.keywordPlusFUNCTIONALIZATION-
dc.subject.keywordPlusCARBOAMINATION-
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 9 items in WoS Click to see citing articles in records_button

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0