Oxoammonium-Catalyzed Oxidation of <i>N</i> -Substituted Amines

We report the development of oxoammonium-catalyzed oxidation of <i>N</i>-substituted amines via a hydride transfer mechanism. Steric and electronic tuning of catalyst led to complementary sets of conditions that can oxidize a broad scope of carbamates, sulfonamides, ureas, and amides into the corresponding imides. The reaction was further demonstrated on a 100-g scale using a continuous flow setup.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2024-11-11
DOI
https://doi.org/10.1021/jacs.4c11758
Citations
10
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
2.50

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article

Oxoammonium-Catalyzed Oxidation of N -Substituted Amines

Frédéric G. Buono, Bartosz Górski, Zhen Lei, Jonas Rein et al.
10 citations
Journal of the American Chemical Society
Oxidative Organic Chemistry Reactions
2.50
article

Oxoammonium-Catalyzed Oxidation of N -Substituted Amines

Frédéric G. Buono, Bartosz Górski, Zhen Lei, Jonas Rein, Song Lin, Yukun Cheng
article en
10 citations

Abstract

We report the development of oxoammonium-catalyzed oxidation of <i>N</i>-substituted amines via a hydride transfer mechanism. Steric and electronic tuning of catalyst led to complementary sets of conditions that can oxidize a broad scope of carbamates, sulfonamides, ureas, and amides into the corresponding imides. The reaction was further demonstrated on a 100-g scale using a continuous flow setup.

Journal of the American Chemical SocietyVol. 146(46)
Cornell University (US), Boehringer Ingelheim (United States) (US)
Boehringer Ingelheim, Camille and Henry Dreyfus Foundation, National Institute of General Medical Sciences
Clean water and sanitation
Openalex Percentile: Top 11%
Oxidative Organic Chemistry Reactions
2.50
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