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

Nicholas A. Falcone; Sam He; John F. Hoskin; Sandeep Mangat; Erik J. Sorensen

doi:10.1021/acs.orglett.4c01263

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

Nicholas A. Falcone, Sam He, John F. Hoskin, Sandeep Mangat, Erik J. Sorensen

Chemistry

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4280-4285
Number of pages	6
Journal	Organic letters
Volume	26
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.4c01263
State	Published - May 24 2024

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c01263

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abstract = "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.",

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AU - Falcone, Nicholas A.

AU - He, Sam

AU - Hoskin, John F.

AU - Mangat, Sandeep

AU - Sorensen, Erik J.

PY - 2024/5/24

Y1 - 2024/5/24

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AB - 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.

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

Abstract

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