Diversification of Amidyl Radical Intermediates Derived from C–H Aminopyridylation

The N-activating substituents typically encountered in C–H amination chemistry are challenging to remove and have limited scope for synthetic elaboration. Here, we demonstrate that N-benzylaminopyridinium species provide a platform for synthetic elaboration via reductive N–N bond activation to unvei...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 14; pp. 2762 - 2766
Main Authors Maity, Asim, Roychowdhury, Pritam, Herrera, Roberto G, Powers, David C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.04.2022
Amer Chemical Soc
Subjects
Amination
Catalysis
Chemistry
Chemistry, Organic
Ethers - chemistry
Ketones - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
HETEROCYCLES
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Summary:The N-activating substituents typically encountered in C–H amination chemistry are challenging to remove and have limited scope for synthetic elaboration. Here, we demonstrate that N-benzylaminopyridinium species provide a platform for synthetic elaboration via reductive N–N bond activation to unveil electrophilic N-centered radicals. These reactive intermediates can be trapped either via anti-Markovnikov olefin carboamination to provide access to tetrahydroisoquinolines or via aza-Rubottom chemistry with silyl enol ethers to provide α-amino ketones.
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These authors contributed equally.
The manuscript was written through contributions of all authors.
Author Contributions
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c00869