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DOI | 10.1126/science.aau1777 |
Ketyl radical reactivity via atom transfer catalysis | |
Wang, Lu; Lear, Jeremy M.; Rafferty, Sean M.; Fosu, Stacy C.; Nagib, David A. | |
2018-10-12 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 362期号:6411页码:225-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | Single-electron reduction of a carbonyl to a ketyl enables access to a polarity-reversed platform of reactivity for this cornerstone functional group. However, the synthetic utility of the ketyl radical is hindered by the strong reductants necessary for its generation, which also limit its reactivity to net reductive mechanisms. We report a strategy for net redox-neutral generation and reaction of ketyl radicals. The in situ conversion of aldehydes to alpha-acetoxy iodides lowers their reduction potential by more than 1 volt, allowing for milder access to the corresponding ketyl radicals and an oxidative termination event. Upon subjecting these iodides to a dimanganese decacarbonyl precatalyst and visible light irradiation, an atom transfer radical addition (ATRA) mechanism affords a broad scope of vinyl iodide products with high Z-selectivity. |
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:000447337200055 |
WOS关键词 | VISIBLE-LIGHT ; SAMARIUM(II) IODIDE ; ORGANIC-SYNTHESIS ; DUAL-CATALYSIS ; CYCLIZATIONS ; HALIDES ; POLYMERIZATION ; ALKENYL |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
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/199813 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | Ohio State Univ, Dept Chem & Biochem, Columbus, OH 43210 USA |
推荐引用方式 GB/T 7714 | Wang, Lu,Lear, Jeremy M.,Rafferty, Sean M.,et al. Ketyl radical reactivity via atom transfer catalysis[J]. SCIENCE,2018,362(6411):225-+. |
APA | Wang, Lu,Lear, Jeremy M.,Rafferty, Sean M.,Fosu, Stacy C.,&Nagib, David A..(2018).Ketyl radical reactivity via atom transfer catalysis.SCIENCE,362(6411),225-+. |
MLA | Wang, Lu,et al."Ketyl radical reactivity via atom transfer catalysis".SCIENCE 362.6411(2018):225-+. |
条目包含的文件 | 条目无相关文件。 |
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