DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kim, Hong Ki | ko |
dc.contributor.author | Mane, Manoj, V | ko |
dc.contributor.author | Montgomery, John | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.date.accessioned | 2019-09-10T05:20:09Z | - |
dc.date.available | 2019-09-10T05:20:09Z | - |
dc.date.created | 2019-09-09 | - |
dc.date.created | 2019-09-09 | - |
dc.date.issued | 2019-07 | - |
dc.identifier.citation | CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.40, pp.9456 - 9463 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10203/267450 | - |
dc.description.abstract | A 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.language | English | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.title | The Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes | - |
dc.type | Article | - |
dc.identifier.wosid | 000482329000020 | - |
dc.identifier.scopusid | 2-s2.0-85065094868 | - |
dc.type.rims | ART | - |
dc.citation.volume | 25 | - |
dc.citation.issue | 40 | - |
dc.citation.beginningpage | 9456 | - |
dc.citation.endingpage | 9463 | - |
dc.citation.publicationname | CHEMISTRY-A EUROPEAN JOURNAL | - |
dc.identifier.doi | 10.1002/chem.201900673 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Mane, Manoj, V | - |
dc.contributor.nonIdAuthor | Montgomery, John | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article; Proceedings Paper | - |
dc.subject.keywordAuthor | borylation | - |
dc.subject.keywordAuthor | copper catalysis | - |
dc.subject.keywordAuthor | cyanation | - |
dc.subject.keywordAuthor | density functional theory | - |
dc.subject.keywordAuthor | selectivities | - |
dc.subject.keywordAuthor | trifunctionalization | - |
dc.subject.keywordPlus | SOLVATION FREE-ENERGIES | - |
dc.subject.keywordPlus | C-H CYANATION | - |
dc.subject.keywordPlus | MOLECULAR CALCULATIONS | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | HYDROBORATION | - |
dc.subject.keywordPlus | ALKENES | - |
dc.subject.keywordPlus | 1,2,3-TRIFUNCTIONALIZATION | - |
dc.subject.keywordPlus | ADDITIONS | - |
dc.subject.keywordPlus | MODEL | - |
dc.subject.keywordPlus | BORON | - |
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