期刊
SCIENCE
卷 362, 期 6413, 页码 434-438出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aat3863
关键词
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资金
- Max Planck Society
- Max-Planck-Institut fur Kohlenforschung
- European Research Commission [ShuttleCat 757608]
- ETH Zurich
- Fonds der Chemischen Industrie
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.
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