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DOI | 10.1126/science.aaw3913 |
Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis | |
Yao, Chengbo1; Dahmen, Tobias2; Gansaeuer, Andreas3; Norton, Jack1 | |
2019-05-24 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 364期号:6442页码:764-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA; Switzerland; Germany |
英文摘要 | The opening of epoxides typically requires electrophilic activation, and subsequent nucleophilic (S(N)2) attack on the less substituted carbon leads to alcohols with Markovnikov regioselectivity. We describe a cooperative catalysis approach to anti-Markovnikov alcohols by combining titanocene-catalyzed epoxide opening with chromium-catalyzed hydrogen activation and radical reduction. The titanocene enforces the anti-Markovnikov regioselectivity by forming the more highly substituted radical. The chromium catalyst sequentially transfers a hydrogen atom, proton, and electron from molecular hydrogen, avoiding a hydride transfer to the undesired site and resulting in 100% atom economy. Each step of the interconnected catalytic cycles was confirmed separately. |
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:000469296000040 |
WOS关键词 | LITHIUM ALUMINUM-HYDRIDE ; CENTER-DOT TRANSFER ; ASYMMETRIC HYDROBORATION ; ORGANIC-SYNTHESIS ; ALLYL ALCOHOLS ; ATOM TRANSFER ; METAL ; REDUCTION ; HYDRATION ; KINETICS |
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/201479 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Columbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA; 2.Dottikon Exclus Synth AG, Hembrunnstr 17, CH-5605 Dottikon, Switzerland; 3.Univ Bonn, Kekule Inst Organ Chem & Biochem, Gerhard Domagk Str 1, D-53121 Bonn, Germany |
推荐引用方式 GB/T 7714 | Yao, Chengbo,Dahmen, Tobias,Gansaeuer, Andreas,et al. Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis[J]. SCIENCE,2019,364(6442):764-+. |
APA | Yao, Chengbo,Dahmen, Tobias,Gansaeuer, Andreas,&Norton, Jack.(2019).Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis.SCIENCE,364(6442),764-+. |
MLA | Yao, Chengbo,et al."Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis".SCIENCE 364.6442(2019):764-+. |
条目包含的文件 | 条目无相关文件。 |
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