Publication: Practical and regioselective amination of arenes using alkyl amines
Authors
Ruffoni, Alessandro ; Juliá Hernández, Fabio ; Svejstrup, Thomas D. ; McMillan, Alistair J. ; Douglas, James J. ; Leonori, Daniele
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Publisher
Nature Research
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DOI
https://doi.org/10.1038/s41557-019-0254-5
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info:eu-repo/semantics/article
Description
© 2019 Crown. 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 Chemistry. To access the final edited and published work see https://doi.org/10.1038/s41557-019-0254-5
Abstract
The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.
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Citation
Nature Chemistry, 2019, Vol. 11, pp. 426-433
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