N‑Oxide-to-Carbon Transmutations of Azaarene N‑Oxides

Reactions that change the identity of an atom within a ring system are emerging as valuable tools for the site-selective editing of molecular structures. Herein, we describe the expansion of an underdeveloped transformation that directly converts azaarene-derived N-oxides to all-carbon arenes. This...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (20), p.4280-4285
Main Authors: Falcone, Nicholas A., He, Sam, Hoskin, John F., Mangat, Sandeep, Sorensen, Erik J.
Format: Article
Language:English
Subjects:
aromatic hydrocarbons
carbon
isotope labeling
moieties
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Summary:Reactions that change the identity of an atom within a ring system are emerging as valuable tools for the site-selective editing of molecular structures. Herein, we describe the expansion of an underdeveloped transformation that directly converts azaarene-derived N-oxides to all-carbon arenes. This ring transmutation exhibits good functional group tolerance and replaces the N-oxide moiety with either unsubstituted, substituted, or isotopically labeled carbon atoms in a single laboratory operation.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01263