ChemInform Abstract: Oxidative Amidation of Nitroalkanes with Amine Nucleophiles Using Molecular Oxygen and Iodine.

Li, Jing; Lear, Martin J.; Kawamoto, Yuya; Umemiya, Shigenobu; Wong, Alice R.; Kwon, Eunsang; Sato, Iwao; Hayashi, Yujiro

doi:10.1002/chin.201611061

ChemInform

2016

DOI: 10.1002/chin.201611061

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ChemInform Abstract: Oxidative Amidation of Nitroalkanes with Amine Nucleophiles Using Molecular Oxygen and Iodine.

Jing Li

Martin J. Lear

Yuya Kawamoto

et al.

Abstract: The title reaction becomes possible in the presence of molecular oxygen and either NIS or I2.

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2022

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“…Chemoselective amidations are particularly useful, and this method provides the amide derived exclusively from Nhydroxyl amines (Scheme 1, 8 → 9, 10 → 11). Finally, some reactions of cyclopropyl-substituted bromonitromethane are not stereospecific, 22 but use of α-fluoro nitronate 5a in these studies led to N-aryl amide 7o as a single diastereomer. Intramolecular cyclization by Michael addition followed N-aryl amide formation in the case leading to 7u due to the electrophilic enoate functionality.…”

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Preparation of N-Aryl Amides by Epimerization-Free Umpolung Amide Synthesis

2022

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Amide synthesis is one of the most widely practiced chemical reactions, owing to its use in drug development and peptide synthesis. Despite the importance of these applications, the attendant effort to eliminate waste associated with these protocols has met with limited success, and pernicious α-epimerization is most often minimized but not eliminated when targeting challenging amides (e.g., N-aryl amides). This effort has focused on what is essentially a single paradigm in amide formation wherein an electrophilic acyl donor reacts with a nucleophilic amine. Umpolung amide synthesis (UmAS) emerged from α-halo nitroalkane reactions with amines and has since been developed into a method for the synthesis of enantiopure amides using entirely catalytic, enantioselective synthesis. However, its inability to forge N-aryl amides has been a longstanding problem, one limiting its application more broadly in drug development where α-chiral N-aryl amides are increasingly common. We report here the reaction of αfluoronitroalkanes and N-aryl hydroxyl amines for the direct synthesis of N-aryl amides using a simple Brønsted base as the promoter. No other activating agents are required, and experiments guided by mechanistic hypotheses outline a mechanism based on the UmAS paradigm and confirm that the N-aryl amide, not the N-aryl hydroxamic acid, is the direct product. Ultimately, select chiral α-amino-N-aryl amides were prepared with complete conservation of enantioenrichment, in contrast to a parallel demonstration of their ability to epimerize using the conventional amide synthesis alternative.

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confidence: 98%

Preparation of N-Aryl Amides by Epimerization-Free Umpolung Amide Synthesis

2022

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ChemInform Abstract: Oxidative Amidation of Nitroalkanes with Amine Nucleophiles Using Molecular Oxygen and Iodine.

Abstract: The title reaction becomes possible in the presence of molecular oxygen and either NIS or I2.

Cited by 1 publication

References 1 publication

Preparation of N-Aryl Amides by Epimerization-Free Umpolung Amide Synthesis

Preparation of N-Aryl Amides by Epimerization-Free Umpolung Amide Synthesis

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