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Verfasst von:Wang, Tao [VerfasserIn]   i
 Stein, Philipp [VerfasserIn]   i
 Shi, Hongwei [VerfasserIn]   i
 Hu, Chao [VerfasserIn]   i
 Rudolph, Matthias [VerfasserIn]   i
 Hashmi, A. Stephen K. [VerfasserIn]   i
Titel:Hydroxylamine-mediated C-C amination via an aza-hock rearrangement
Verf.angabe:Tao Wang, Philipp M. Stein, Hongwei Shi, Chao Hu, Matthias Rudolph & A. Stephen K. Hashmi
E-Jahr:2021
Jahr:02 December 2021
Umfang:11 S.
Fussnoten:Gesehen am 17.12.2021
Titel Quelle:Enthalten in: Nature Communications
Ort Quelle:[London] : Nature Publishing Group UK, 2010
Jahr Quelle:2021
Band/Heft Quelle:12(2021), Artikel-ID 7029, Seite 1-11
ISSN Quelle:2041-1723
Abstract:Despite the widespread use of anilines, synthetic challenges to these targets still exist. Selectivity is often an issue, when using the traditional nitration-reduction sequence or more modern approaches, including arene C-H aminations catalyzed by transition metals, photosensitizers, or electrodes. Accordingly, there is still a need for general methods to rapidly, directly access specific isomers of substituted anilines. Here, we report a simple route towards the synthesis of such motifs starting from benzyl alcohols, which are converted to anilines by the use of arylsulfonyl hydroxylamines, via an aza-Hock rearrangement. Good to excellent yields are observed. The method is applicable to various benzyl alcohol surrogates (such as ethers, esters, and halides) as well as simple alkylarenes. Functionalizations of pharmaceutically relevant structures are feasible under the reaction conditions. Over ten amination reagents can be used, which facilitates the rapid assembly of a vast set of compounds.
DOI:doi:10.1038/s41467-021-27271-y
URL:kostenfrei: Volltext: https://doi.org/10.1038/s41467-021-27271-y
 kostenfrei: Volltext: https://www.nature.com/articles/s41467-021-27271-y
 DOI: https://doi.org/10.1038/s41467-021-27271-y
Datenträger:Online-Ressource
Sprache:eng
Sach-SW:Chemical synthesis
 Synthetic chemistry methodology
K10plus-PPN:1782428674
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