DC Field | Value | Language |
---|---|---|
dc.contributor.author | PARK, YOONSU | ko |
dc.contributor.author | Park, Kyung Tae | ko |
dc.contributor.author | Kim, Jeung Gon | ko |
dc.contributor.author | Chang, Suk-Bok | ko |
dc.date.accessioned | 2015-11-20T09:03:36Z | - |
dc.date.available | 2015-11-20T09:03:36Z | - |
dc.date.created | 2015-05-12 | - |
dc.date.created | 2015-05-12 | - |
dc.date.created | 2015-05-12 | - |
dc.date.created | 2015-05-12 | - |
dc.date.created | 2015-05-12 | - |
dc.date.created | 2015-05-12 | - |
dc.date.issued | 2015-04 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.137, no.13, pp.4534 - 4542 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/200980 | - |
dc.description.abstract | Mechanistic investigations on the Cp*Rh(III)-catalyzed direct C-H amination reaction led us to reveal the new utility of 1,4,2-dioxazol-5-one and its derivatives as highly efficient amino sources. Stepwise analysis on the C-N bond-forming process showed that competitive binding of rhodium metal center to amidating reagent or substrate is closely related to the reaction efficiency. In this line, 1,4,2-dioxazol-5-ones were observed to have a strong affinity to the cationic Rh(III) giving rise to dramatically improved amidation efficiency when compared to azides. Kinetics and computational studies suggested that the high amidating reactivity of 1,4,2-dioxazol-5-one can also be attributed to the low activation energy of an imido-insertion process in addition to the high coordination ability. While the characterization of a cationic Cp*Rh(III) complex bearing an amidating reagent was achieved, its facile conversion to an amido-inserted rhodacycle allowed for a clear picture on the C-H amidation process. The newly developed amidating reagent of 1,4,2-dioxazol-5-ones was applicable to a broad range of substrates with high functional group tolerance, releasing carbon dioxide as a single byproduct. Additional attractive features of this amino source, such as they are more convenient to prepare, store, and use when compared to the corresponding azides, take a step closer toward an ideal C-H amination protocol. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C-H Amination with a New Type of Amidating Reagent | - |
dc.type | Article | - |
dc.identifier.wosid | 000352752000039 | - |
dc.identifier.scopusid | 2-s2.0-84926648683 | - |
dc.type.rims | ART | - |
dc.citation.volume | 137 | - |
dc.citation.issue | 13 | - |
dc.citation.beginningpage | 4534 | - |
dc.citation.endingpage | 4542 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.5b01324 | - |
dc.contributor.localauthor | PARK, YOONSU | - |
dc.contributor.localauthor | Chang, Suk-Bok | - |
dc.contributor.nonIdAuthor | Park, Kyung Tae | - |
dc.contributor.nonIdAuthor | Kim, Jeung Gon | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | N BOND FORMATION | - |
dc.subject.keywordPlus | CARBON-NITROGEN BONDS | - |
dc.subject.keywordPlus | SULFONYL AZIDES | - |
dc.subject.keywordPlus | INTERMOLECULAR AMIDATION | - |
dc.subject.keywordPlus | COUPLING REACTIONS | - |
dc.subject.keywordPlus | FORMING REACTIONS | - |
dc.subject.keywordPlus | AROMATIC KETONES | - |
dc.subject.keywordPlus | NATURAL-PRODUCTS | - |
dc.subject.keywordPlus | SYNTHETIC ROUTE | - |
dc.subject.keywordPlus | ATOM-TRANSFER | - |
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