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Mechanistic Studies of the Rhodium-Catalyzed Direct C–H Amination Reaction Using Azides as the Nitrogen Source : Mechanistic Studies of the Rhodium-Catalyzed Direct C-H Amination Reaction Using Azides as the Nitrogen Source
DC Field | Value | Language |
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dc.contributor.author | Park, Sae Hume | - |
dc.contributor.author | Kwak, Jaesung | - |
dc.contributor.author | Shin, Kwangmin | - |
dc.contributor.author | Ryu, Jaeyune | - |
dc.contributor.author | Park, Yoonsu | - |
dc.contributor.author | Chang, Sukbok | - |
dc.date.accessioned | 2023-05-03T05:46:57Z | - |
dc.date.available | 2023-05-03T05:46:57Z | - |
dc.date.created | 2023-05-01 | - |
dc.date.created | 2023-05-01 | - |
dc.date.created | 2023-05-01 | - |
dc.date.issued | 2014-02 | - |
dc.identifier.citation | Journal of the American Chemical Society, Vol.136 No.6, pp.2492-2502 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://hdl.handle.net/10371/191820 | - |
dc.description.abstract | Direct C-H amination of arenes offers a straightforward route to aniline compounds without necessitating aryl (pseudo)halides as the starting materials. The recent development in this area, in particular in the metal-mediated transformations, is significant with regard to substrate scope and reaction conditions. Described herein are the mechanistic details on the Rh-catalyzed direct C-H amination reaction using organic azides as the amino source. The most important two stages were investigated especially in detail: (i) the formation of metal nitrenoid species and its subsequent insertion into a rhodacycle intermediate, and (ii) the regeneration of catalyst with concomitant release of products. It was revealed that a stepwise pathway involving a key Rh(V)-nitrenoid species that subsequently undergoes amido insertion is favored over a concerted C-N bond formation pathway. DFT calculations and kinetic studies suggest that the rate-limiting step in the current C-H amination reaction is more closely related to the formation of Rh nitrenoid intermediate rather than the presupposed C-H activation process. The present study provides mechanistic details of the direct C-H amination reaction, which bears both aspects of the inner- and outer-sphere paths within a catalytic cycle. | - |
dc.language | 영어 | - |
dc.publisher | American Chemical Society | - |
dc.title | Mechanistic Studies of the Rhodium-Catalyzed Direct C–H Amination Reaction Using Azides as the Nitrogen Source | - |
dc.title.alternative | Mechanistic Studies of the Rhodium-Catalyzed Direct C-H Amination Reaction Using Azides as the Nitrogen Source | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/ja411072a | - |
dc.citation.journaltitle | Journal of the American Chemical Society | - |
dc.identifier.wosid | 000331343300048 | - |
dc.identifier.scopusid | 2-s2.0-84894184671 | - |
dc.citation.endpage | 2502 | - |
dc.citation.number | 6 | - |
dc.citation.startpage | 2492 | - |
dc.citation.volume | 136 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Ryu, Jaeyune | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | N BOND FORMATION | - |
dc.subject.keywordPlus | INDUCED REDUCTIVE ELIMINATIONS | - |
dc.subject.keywordPlus | ARYL AZIDES | - |
dc.subject.keywordPlus | INTERMOLECULAR AMINATION | - |
dc.subject.keywordPlus | INTRAMOLECULAR AMIDATION | - |
dc.subject.keywordPlus | HETEROCYCLE SYNTHESIS | - |
dc.subject.keywordPlus | IMIDOMETAL COMPLEXES | - |
dc.subject.keywordPlus | CONVENIENT SYNTHESIS | - |
dc.subject.keywordPlus | ANILINE DERIVATIVES | - |
dc.subject.keywordPlus | ORGANIC AZIDES | - |
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