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DOI | 10.1126/science.aat3863 |
Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes | |
Legnani, Luca1; Prina-Cerai, Gabriele1; Delcaillau, Tristan1,2; Willems, Suzanne1; Morandi, Bill1,2 | |
2018-10-26 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 362期号:6413页码:434-438 |
文章类型 | Article |
语种 | 英语 |
国家 | Germany; Switzerland |
英文摘要 | Primary amines are essential constituents of biologically active molecules and versatile intermediates in the synthesis of drugs and agrochemicals. However, their preparation from easily accessible alkenes remains challenging. Here, we report a general strategy to access primary amines from alkenes through an operationally simple iron-catalyzed aminochlorination reaction. A stable hydroxylamine derivative and benign sodium chloride act as the respective nitrogen and chlorine sources. The reaction proceeds at room temperature under air; tolerates a large scope of aliphatic and conjugated alkenes, including densely functionalized substrates; and provides excellent anti-Markovnikov regioselectivity with respect to the amino group. The reactivity of the 2-chloroalkylamine products, an understudied class of amphoteric molecules, enables facile access to linear or branched aliphatic amines, aziridines, aminonitriles, azido amines, and homoallylic amines. |
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:000450441900044 |
WOS关键词 | STEREOSPECIFIC SYNTHESIS ; UNACTIVATED OLEFINS ; N-H ; AZIRIDINES ; AMINATION ; CHEMISTRY ; AMMONIA ; ION ; HYDROAMINATION ; DIAZIDATION |
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/199929 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Max Planck Inst Kohlenforsch, Mulheim, Germany; 2.Swiss Fed Inst Technol, Zurich, Switzerland |
推荐引用方式 GB/T 7714 | Legnani, Luca,Prina-Cerai, Gabriele,Delcaillau, Tristan,et al. Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes[J]. SCIENCE,2018,362(6413):434-438. |
APA | Legnani, Luca,Prina-Cerai, Gabriele,Delcaillau, Tristan,Willems, Suzanne,&Morandi, Bill.(2018).Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes.SCIENCE,362(6413),434-438. |
MLA | Legnani, Luca,et al."Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes".SCIENCE 362.6413(2018):434-438. |
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