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Copper-catalysed amination of alkyl iodides enabled by halogen-atom transfer

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dc.contributor.authorGorski, Bartosz
dc.contributor.authorBarthelemy, Anne-Laure
dc.contributor.authorDouglas, James J.
dc.contributor.authorJuliá Hernández, Fabio
dc.contributor.authorLeonori, Daniele
dc.contributor.departmentQuímica Inorgánica
dc.date.accessioned2025-01-24T11:36:10Z
dc.date.available2025-01-24T11:36:10Z
dc.date.issued2021-07-12
dc.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
dc.description.abstractDespite 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.
dc.formatapplication/pdfes
dc.format.extent15
dc.identifier.citationNature Catalysis, 2021, Vol. 4, pp. 623–630
dc.identifier.doihttps://doi.org/10.1038/s41929-021-00652-8
dc.identifier.issnElectronic: 2520-1158
dc.identifier.urihttp://hdl.handle.net/10201/149196
dc.languageenges
dc.publisherNature Research
dc.relationD. L. thanks EPSRC for a Fellowship (EP/P004997/1) and a Research Grant (EP/T016019/1) and the European Research Council for a research grant (758427).es
dc.relation.publisherversionhttps://www.nature.com/articles/s41929-021-00652-8
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectHomogeneous catalysis
dc.subjectSynthetic chemistry methodology
dc.titleCopper-catalysed amination of alkyl iodides enabled by halogen-atom transferes
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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