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DOI | 10.1126/science.aav5606 |
Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry | |
Peters, Byron K.1; Rodriguez, Kevin X.1; Reisberg, Solomon H.1; Beil, Sebastian B.1; Hickey, David P.2; Kawamata, Yu1; Collins, Michael3; Starr, Jeremy3; Chen, Longrui4; Udyavara, Sagar5; Klunder, Kevin2; Gorey, Timothy J.2; Anderson, Scott L.2; Neurock, Matthew5; Minteer, Shelley D.2; Baran, Phil S.1 | |
2019-02-22 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 363期号:6429页码:838-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA; Peoples R China |
英文摘要 | Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino) phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal-type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings. |
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:000459387100037 |
WOS关键词 | DISSOLVING METAL REDUCTION ; MOLECULAR-ORBITAL METHODS ; FINDING SADDLE-POINTS ; SOLVATED ELECTRONS ; AROMATIC-COMPOUNDS ; SILICA-GEL ; ELECTROCHEMICAL REDUCTION ; BIRCH REDUCTION ; ULTRASOFT PSEUDOPOTENTIALS ; CRYSTAL-STRUCTURE |
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/200810 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Scripps Res, Dept Chem, La Jolla, CA 92037 USA; 2.Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA; 3.Pfizer Global Res & Dev, Med Design, Discovery Sci, Groton, CT 06340 USA; 4.Tianjin Econ Technol Dev Zone, Asymchem Life Sci Tianjin, Tianjin 300457, Peoples R China; 5.Univ Minnesota, Dept Chem Engn & Mat Sci, 421 Washington Ave SE, Minneapolis, MN 55455 USA |
推荐引用方式 GB/T 7714 | Peters, Byron K.,Rodriguez, Kevin X.,Reisberg, Solomon H.,et al. Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry[J]. SCIENCE,2019,363(6429):838-+. |
APA | Peters, Byron K..,Rodriguez, Kevin X..,Reisberg, Solomon H..,Beil, Sebastian B..,Hickey, David P..,...&Baran, Phil S..(2019).Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry.SCIENCE,363(6429),838-+. |
MLA | Peters, Byron K.,et al."Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry".SCIENCE 363.6429(2019):838-+. |
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