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DOI | 10.1126/science.aap7503 |
Selective formation of gamma-lactams via C-H amidation enabled by tailored iridium catalysts | |
Hong, Seung Youn; Park, Yoonsu; Hwang, Yeongyu; Kim, Yeong Bum; Baik, Mu-Hyun1; Chang, Sukbok1 | |
2018-03-02 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 359期号:6379页码:1016-1021 |
文章类型 | Article |
语种 | 英语 |
国家 | South Korea |
英文摘要 | 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. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000426366200038 |
WOS关键词 | AMINATION REACTIONS ; BOND AMINATION ; AMIDO TRANSFER ; ARYL AZIDES ; PORPHYRINS ; COMPLEXES ; RUTHENIUM ; OXIDATION ; ALKENES ; AMINES |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/198091 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Korea Adv Inst Sci & Technol, Dept Chem, Daejeon 34141, South Korea; 2.Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Daejeon 34141, South Korea |
推荐引用方式 GB/T 7714 | Hong, Seung Youn,Park, Yoonsu,Hwang, Yeongyu,et al. Selective formation of gamma-lactams via C-H amidation enabled by tailored iridium catalysts[J]. SCIENCE,2018,359(6379):1016-1021. |
APA | Hong, Seung Youn,Park, Yoonsu,Hwang, Yeongyu,Kim, Yeong Bum,Baik, Mu-Hyun,&Chang, Sukbok.(2018).Selective formation of gamma-lactams via C-H amidation enabled by tailored iridium catalysts.SCIENCE,359(6379),1016-1021. |
MLA | Hong, Seung Youn,et al."Selective formation of gamma-lactams via C-H amidation enabled by tailored iridium catalysts".SCIENCE 359.6379(2018):1016-1021. |
条目包含的文件 | 条目无相关文件。 |
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