Publication: Copper-catalysed amination of alkyl iodides enabled by halogen-atom transfer
Authors
Gorski, Bartosz ; Barthelemy, Anne-Laure ; Douglas, James J. ; Juliá Hernández, Fabio ; Leonori, Daniele
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Publisher
Nature Research
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DOI
https://doi.org/10.1038/s41929-021-00652-8
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info:eu-repo/semantics/article
Description
© 2021, The Author(s), under exclusive licence to Springer Nature Limited. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Nature Catalysis. To access the final edited and published work see https://doi.org/10.1038/s41929-021-00652-8
Abstract
Despite the fact that nucleophilic displacement (SN2) of alkyl halides with nitrogen nucleophiles is one of the first reactions introduced in organic chemistry teaching, its practical utilization is largely limited to unhindered (primary) or activated (α-carbonyl, benzylic) substrates. Here, we demonstrate an alternative amination strategy where alkyl iodides are used as radical precursors instead of electrophiles. Use of α-aminoalkyl radicals enables the efficient conversion of the iodides into the corresponding alkyl radical by halogen-atom transfer, while copper catalysis assembles the sp3 C–N bonds at room temperature. The process provides SN2-like programmability, and application in late-stage functionalization of several densely functionalized pharmaceuticals demonstrates its utility in the preparation of valuable N-alkylated drug analogues.
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Citation
Nature Catalysis, 2021, Vol. 4, pp. 623–630
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