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Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes

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Legnani,  Luca
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Prina Cerai,  Gabriele
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Delcaillau,  Tristan
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
ETH Zürich;

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Willems,  Suzanne
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
ETH Zürich;

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Citation

Legnani, L., Prina Cerai, G., Delcaillau, T., Willems, S., & Morandi, B. (2018). Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes. Science, 362(6413), 434-438. doi:10.1126/science.aat3863.


Cite as: http://hdl.handle.net/21.11116/0000-0002-A153-A
Abstract
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.