DC Field | Value | Language |
---|---|---|
dc.contributor.author | Jeon, Jinwon | ko |
dc.contributor.author | Ryu, Ho | ko |
dc.contributor.author | Lee, Changseok | ko |
dc.contributor.author | Cho, Dasol | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Hong, Sungwoo | ko |
dc.date.accessioned | 2019-07-22T05:10:06Z | - |
dc.date.available | 2019-07-22T05:10:06Z | - |
dc.date.created | 2019-07-02 | - |
dc.date.created | 2019-07-02 | - |
dc.date.issued | 2019-06 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.25, pp.10048 - 10059 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/263682 | - |
dc.description.abstract | A 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.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Site-Selective 1,1-Difunctionalization of Unactivated Alkenes Enabled by Cationic Palladium Catalysis | - |
dc.type | Article | - |
dc.identifier.wosid | 000473251500041 | - |
dc.identifier.scopusid | 2-s2.0-85067998374 | - |
dc.type.rims | ART | - |
dc.citation.volume | 141 | - |
dc.citation.issue | 25 | - |
dc.citation.beginningpage | 10048 | - |
dc.citation.endingpage | 10059 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.9b04142 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.localauthor | Hong, Sungwoo | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | C-H ACTIVATION | - |
dc.subject.keywordPlus | ORGANOBORONIC ACIDS | - |
dc.subject.keywordPlus | INTERMOLECULAR AMINOACETOXYLATION | - |
dc.subject.keywordPlus | CYCLIZATION REACTION | - |
dc.subject.keywordPlus | C(SP(3))-H BONDS | - |
dc.subject.keywordPlus | TERMINAL ALKENES | - |
dc.subject.keywordPlus | DIFUNCTIONALIZATION | - |
dc.subject.keywordPlus | CONSTRUCTION | - |
dc.subject.keywordPlus | FUNCTIONALIZATION | - |
dc.subject.keywordPlus | CARBOAMINATION | - |
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