Site-Selective 1,1-Difunctionalization of Unactivated Alkenes Enabled by Cationic Palladium Catalysis
DC Field | Value | Language |
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dc.contributor.author | Jinwon Jeon | - |
dc.contributor.author | Ho Ryu | - |
dc.contributor.author | Changseok Lee | - |
dc.contributor.author | Dasol Cho | - |
dc.contributor.author | Mu-Hyun Baik | - |
dc.contributor.author | Sungwoo Hong | - |
dc.date.available | 2019-08-21T06:20:26Z | - |
dc.date.created | 2019-07-23 | - |
dc.date.issued | 2019-06 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/6067 | - |
dc.description.abstract | © 2019 American Chemical Society.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 β-hydride elimination and migratory insertion with a cationic palladium catalyst. The resulting η3-π-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 γ,γ- or δ,δ-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.description.uri | 1 | - |
dc.language | 영어 | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Site-Selective 1,1-Difunctionalization of Unactivated Alkenes Enabled by Cationic Palladium Catalysis | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 000473251500041 | - |
dc.identifier.scopusid | 2-s2.0-85067998374 | - |
dc.identifier.rimsid | 68995 | - |
dc.contributor.affiliatedAuthor | Jinwon Jeon | - |
dc.contributor.affiliatedAuthor | Ho Ryu | - |
dc.contributor.affiliatedAuthor | Changseok Lee | - |
dc.contributor.affiliatedAuthor | Dasol Cho | - |
dc.contributor.affiliatedAuthor | Mu-Hyun Baik | - |
dc.contributor.affiliatedAuthor | Sungwoo Hong | - |
dc.identifier.doi | 10.1021/jacs.9b04142 | - |
dc.identifier.bibliographicCitation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.25, pp.10048 - 10059 | - |
dc.citation.title | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.volume | 141 | - |
dc.citation.number | 25 | - |
dc.citation.startPage | 10048 | - |
dc.citation.endPage | 10059 | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |