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DOI | 10.1126/science.aan1411 |
A catalytic fluoride-rebound mechanism for C(sp(3))-CF3 bond formation | |
Levin, Mark D.1; 39;Neil, James P.2 | |
2017-06-23 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2017 |
卷号 | 356期号:6344页码:1272-1275 |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | The biological properties of trifluoromethyl compounds have led to their ubiquity in pharmaceuticals, yet their chemical properties have made their preparation a substantial challenge, necessitating innovative chemical solutions. We report the serendipitous discovery of a borane-catalyzed formal C(sp(3))-CF3 reductive elimination from Au(III) that accesses these compounds by a distinct mechanism proceeding via fluoride abstraction, migratory insertion, and C-F reductive elimination to achieve a net C-C bond construction. The parent bis(trifluoromethyl) Au(III) complexes tolerate a surprising breadth of synthetic protocols, enabling the synthesis of complex organic derivatives without cleavage of the Au-C bond. This feature, combined with the "fluoride-rebound" mechanism, was translated into a protocol for the synthesis of F-18-radiolabeled aliphatic CF3-containing compounds, enabling the preparation of potential tracers for use in positron emission tomography. |
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:000403881700037 |
WOS关键词 | FORMING REDUCTIVE ELIMINATION ; POSITRON-EMISSION-TOMOGRAPHY ; LATE-STAGE ; TRIFLUOROMETHYL GROUP ; ARYL IODIDES ; COMPLEXES ; PET ; FLUORINATION ; GOLD(III) ; RADIOSYNTHESIS |
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/196310 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA; 2.Lawrence Berkeley Natl Lab, Div Chem Sci, Berkeley, CA 94720 USA; 3.Lawrence Berkeley Natl Lab, Biomed Isotope Lab, Berkeley, CA 94720 USA |
推荐引用方式 GB/T 7714 | Levin, Mark D.,39;Neil, James P.. A catalytic fluoride-rebound mechanism for C(sp(3))-CF3 bond formation[J]. SCIENCE,2017,356(6344):1272-1275. |
APA | Levin, Mark D.,&39;Neil, James P..(2017).A catalytic fluoride-rebound mechanism for C(sp(3))-CF3 bond formation.SCIENCE,356(6344),1272-1275. |
MLA | Levin, Mark D.,et al."A catalytic fluoride-rebound mechanism for C(sp(3))-CF3 bond formation".SCIENCE 356.6344(2017):1272-1275. |
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