DC Field | Value | Language |
---|---|---|
dc.contributor.author | Hong, Seung Youn | ko |
dc.contributor.author | PARK, YOONSU | ko |
dc.contributor.author | Hwang, Yeongyu | ko |
dc.contributor.author | Kim, Yeong Bum | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Chang, Sukbok | ko |
dc.date.accessioned | 2018-03-23T00:14:17Z | - |
dc.date.available | 2018-03-23T00:14:17Z | - |
dc.date.created | 2018-03-20 | - |
dc.date.created | 2018-03-20 | - |
dc.date.created | 2018-03-20 | - |
dc.date.created | 2018-03-20 | - |
dc.date.created | 2018-03-20 | - |
dc.date.issued | 2018-03 | - |
dc.identifier.citation | SCIENCE, v.359, no.6379, pp.1016 - 1021 | - |
dc.identifier.issn | 0036-8075 | - |
dc.identifier.uri | http://hdl.handle.net/10203/240919 | - |
dc.description.abstract | Intramolecular insertion of metal nitrenes into carbon-hydrogen bonds to form gamma-lactam rings has traditionally been hindered bycompeting isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding gamma-lactams via sp(3) and sp(2) C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules. | - |
dc.language | English | - |
dc.publisher | AMER ASSOC ADVANCEMENT SCIENCE | - |
dc.title | Selective formation of gamma-lactams via C-H amidation enabled by tailored iridium catalysts | - |
dc.type | Article | - |
dc.identifier.wosid | 000426366200038 | - |
dc.identifier.scopusid | 2-s2.0-85042857559 | - |
dc.type.rims | ART | - |
dc.citation.volume | 359 | - |
dc.citation.issue | 6379 | - |
dc.citation.beginningpage | 1016 | - |
dc.citation.endingpage | 1021 | - |
dc.citation.publicationname | SCIENCE | - |
dc.identifier.doi | 10.1126/science.aap7503 | - |
dc.contributor.localauthor | PARK, YOONSU | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.localauthor | Chang, Sukbok | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | AMINATION REACTIONS | - |
dc.subject.keywordPlus | BOND AMINATION | - |
dc.subject.keywordPlus | AMIDO TRANSFER | - |
dc.subject.keywordPlus | ARYL AZIDES | - |
dc.subject.keywordPlus | PORPHYRINS | - |
dc.subject.keywordPlus | COMPLEXES | - |
dc.subject.keywordPlus | RUTHENIUM | - |
dc.subject.keywordPlus | OXIDATION | - |
dc.subject.keywordPlus | ALKENES | - |
dc.subject.keywordPlus | AMINES | - |
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