GSTDTAP  > 地球科学
DOI10.1126/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
ISSN0036-8075
EISSN1095-9203
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
被引频次:94[WOS]   [WOS记录]     [WOS相关记录]
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
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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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