Iodide-umpolung catalytic system for non-traditional amide coupling from nitroalkanes and amines

Chen, Chun-Lin; Huang, Tian-Sih; Chang, Po-Hsiang; Hsu, Che-Sheng

doi:10.1039/d4ob00184b

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00184b

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Iodide-umpolung catalytic system for non-traditional amide coupling from nitroalkanes and amines

Chun-Lin Chen,

Tian-Sih Huang,

Po-Hsiang Chang

et al.

Abstract: An unusual oxidation using an N-iodosuccinimide (NIS) catalyst was developed for use in the nontraditional synthesis of amide derivatives from nitroalkanes and amines. In contrast to traditional oxidative catalysis this...

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Cited by 2 publications

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Facile Access to Terminal Nitroalkanes via Anti‐Markovnikov Hydronitration and Hydronitroalkylation of Alkenes Using Photoredox Catalysis

Patra,

Katayev

2024

Chemistry A European J

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The evolution of catalysis and functional group transfer reagents play a significant role in the development of anti‐Markovnikov alkene hydrofunctionalization reactions, facilitating the access to value‐added molecules. We herein report the first rational design of a modular intermolecular anti‐Markovnikov hydronitration of alkenes, enabling the direct synthesis of terminal nitroalkanes under visible light‐mediated photoredox catalysis. By employing the redox‐active organic nitrating reagent N‐nitrosuccinimide, the produced nitryl radicals, in the presence of an olefin and a hydrogen atom transfer (HAT) mediator, lead to an anti‐Markovnikov addition with complete regioselectivity. Furthermore, we present results demonstrating the use of this catalytic system for chain expansion via anti‐Markovnikov addition, utilizing substituted bromonitroalkanes as commercially available reagents. These transformations effectively address a gap in synthetic chemistry, enabling the direct synthesis of nitroalkanes from a variety of unactivated oleﬁns in both complex molecules and unfunctionalized commodity chemicals.

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Facile Access to Terminal Nitroalkanes via Anti‐Markovnikov Hydronitration and Hydronitroalkylation of Alkenes Using Photoredox Catalysis

Patra,

Katayev

2024

Chemistry A European J

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Synthesis of Polysubstituted Vinyl Sulfones by Direct C−S Cross‐Coupling

Huang,

Chen,

Tsai

et al. 2024

Chemistry A European J

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Vinyl sulfones are valued for their unique chemical properties and bioactivity, but creating a wide range of different analogs remains a challenge. To address this limitation, we have developed a novel approach that facilitates the synthesis of polysubstituted vinyl sulfones. This method utilizes the dual functionality of NIS as a promoter that enables sulfonation and elimination in the synthesis of vinyl sulfones. We used the broad applicability, efficiency, selectivity, and functional group tolerance of this approach to synthesize more than 70 examples. Additionally, competition experiments have provided insights into the reactivity and selectivity of the transient sulfonyl radical towards various C‐C multiple bonds. Herein, we describe using this mild protocol in the late‐stage vinyl sulfonation of complex molecules to simplify the synthesis of specific targets and enable the modification of complex natural products and advanced materials.

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Iodide-umpolung catalytic system for non-traditional amide coupling from nitroalkanes and amines

Abstract: An unusual oxidation using an N-iodosuccinimide (NIS) catalyst was developed for use in the nontraditional synthesis of amide derivatives from nitroalkanes and amines. In contrast to traditional oxidative catalysis this...

Cited by 2 publications

References 33 publications

Facile Access to Terminal Nitroalkanes via Anti‐Markovnikov Hydronitration and Hydronitroalkylation of Alkenes Using Photoredox Catalysis

Facile Access to Terminal Nitroalkanes via Anti‐Markovnikov Hydronitration and Hydronitroalkylation of Alkenes Using Photoredox Catalysis

Synthesis of Polysubstituted Vinyl Sulfones by Direct C−S Cross‐Coupling

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