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DOI | 10.1126/science.aar6117 |
Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction | |
Friedfeld, Max R.1; Zhong, Hongyu1; Ruck, Rebecca T.2; Shevlin, Michael2; Chirik, Paul J.1 | |
2018-05-25 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 360期号:6391页码:888-892 |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | Identifying catalyst activation modes that exploit one-electron chemistry and overcome associated deactivation pathways will be transformative for developing first-row transition metal catalysts with performance equal or, ideally, superior to precious metals. Here we describe a zinc-activation method compatible with high-throughput reaction discovery that identified scores of cobalt-phosphine combinations for the asymmetric hydrogenation of functionalized alkenes. An optimized catalyst prepared from (R, R)-Ph-BPE {Ph-BPE, 1,2bis-[(2R, 5R)-2,5-diphenylphospholano] ethane} and cobalt chloride [CoCl2 center dot 6H(2)O] exhibited high activity and enantioselectivity in protic media and enabled the asymmetric synthesis of the epilepsy medication levetiracetam at 200-gram scale with 0.08 mole % catalyst loading. Stoichiometric studies established that the cobalt (II) catalyst precursor (R, R)-Ph-BPECoCl2 underwent ligand displacement by methanol, and zinc promoted facile one-electron reduction to cobalt (I), which more stably bound the phosphine. |
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:000433039800043 |
WOS关键词 | BIS(PHOSPHINE)COBALT DIALKYL COMPLEXES ; ALKENE HYDROGENATION ; HOMOGENEOUS HYDROGENATION ; OLEFINS ; DISCOVERY ; IRON |
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/198739 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Princeton Univ, Dept Chem, Princeton, NJ 08544 USA; 2.Merck Res Labs, Dept Proc Res & Dev, Rahway, NJ 07065 USA |
推荐引用方式 GB/T 7714 | Friedfeld, Max R.,Zhong, Hongyu,Ruck, Rebecca T.,et al. Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction[J]. SCIENCE,2018,360(6391):888-892. |
APA | Friedfeld, Max R.,Zhong, Hongyu,Ruck, Rebecca T.,Shevlin, Michael,&Chirik, Paul J..(2018).Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction.SCIENCE,360(6391),888-892. |
MLA | Friedfeld, Max R.,et al."Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction".SCIENCE 360.6391(2018):888-892. |
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