DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kim, Hyunwoo | ko |
dc.contributor.author | Heo, Joon | ko |
dc.contributor.author | Kim, Junho | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Chang, Sukbok | ko |
dc.date.accessioned | 2018-12-20T01:48:32Z | - |
dc.date.available | 2018-12-20T01:48:32Z | - |
dc.date.created | 2018-11-26 | - |
dc.date.created | 2018-11-26 | - |
dc.date.issued | 2018-10 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.140, no.43, pp.14350 - 14356 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/247140 | - |
dc.description.abstract | The direct amination of C-H bonds with ammonia is a challenge in synthetic chemistry. Herein, we present a copper-mediated approach that enables a chelation-assisted aromatic C-H bond amination using aqueous ammonia. A key strategy was to use soft low-valent Cu(I) species to avoid the strong coordination of ammonia. Mechanistic investigations suggest that the catalysis is initiated by a facile deprotonation of bound ammonia, and the C-N coupling is achieved by subsequent reductive elimination of the resultant copper-amido intermediate from a Cu(III) intermediate that is readily generated by disproportionation of low-valent copper analogues. This mechanistic postulate was supported by a preliminary kinetic isotope effect study and computations. This new chelation-assisted, copper-mediated C-H bond amination with aqueous ammonia was successfully applied to a broad range of substrates to deliver primary anilines. Moreover, the mild conditions required for this transformation allowed the reaction to operate even under substoichiometric conditions to enable a late-stage application for the preparation of pharmaceutical agents. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | CROSS-COUPLING REACTIONS | - |
dc.subject | CATALYZED AMINATION | - |
dc.subject | PRIMARY AMINES | - |
dc.subject | AMIDATION | - |
dc.subject | PALLADIUM | - |
dc.subject | HYDROGEN | - |
dc.subject | ANILINES | - |
dc.subject | ACTIVATION | - |
dc.subject | COMPLEXES | - |
dc.subject | CLEAVAGE | - |
dc.title | Copper-Mediated Amination of Aryl C-H Bonds with the Direct Use of Aqueous Ammonia via a Disproportionation Pathway | - |
dc.type | Article | - |
dc.identifier.wosid | 000449239700046 | - |
dc.identifier.scopusid | 2-s2.0-85055638839 | - |
dc.type.rims | ART | - |
dc.citation.volume | 140 | - |
dc.citation.issue | 43 | - |
dc.citation.beginningpage | 14350 | - |
dc.citation.endingpage | 14356 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.8b08826 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.localauthor | Chang, Sukbok | - |
dc.contributor.nonIdAuthor | Kim, Hyunwoo | - |
dc.contributor.nonIdAuthor | Heo, Joon | - |
dc.contributor.nonIdAuthor | Kim, Junho | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | CROSS-COUPLING REACTIONS | - |
dc.subject.keywordPlus | CATALYZED AMINATION | - |
dc.subject.keywordPlus | PRIMARY AMINES | - |
dc.subject.keywordPlus | AMIDATION | - |
dc.subject.keywordPlus | PALLADIUM | - |
dc.subject.keywordPlus | HYDROGEN | - |
dc.subject.keywordPlus | ANILINES | - |
dc.subject.keywordPlus | ACTIVATION | - |
dc.subject.keywordPlus | COMPLEXES | - |
dc.subject.keywordPlus | CLEAVAGE | - |
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