Metal‐free Synthesis of <scp>β‐Nitrostyrenes</scp> via <scp>DDQ‐Catalyzed</scp> Nitration

Park, Sangwoon; Yoon, Seungri; Min, Seungjae

doi:10.1002/bkcs.12232

Cited by 6 publications

(1 citation statement)

References 38 publications

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“…Alternatively, the NO 2 . radical can encounter the neutral olefin to provide radical intermediate C , which upon HAT [19] by DDQ* can directly produce 2 (Path B) [20] . However, the substantial luminescence quenching effect displayed by the styrene derivative (Figure 1) and comparatively diminished reactivity of the electron‐deficient double‐bonds towards the nitration reaction advocate for an electron transfer photooxidation of the olefins (Path A) as the major pathway.…”

Section: Methodsmentioning

confidence: 99%

Organophotoredox Catalyzed Stereoselective Nitration of Olefins with tert‐Butyl Nitrite under Air

et al. 2021

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An efficient method for the E-selective synthesis of nitroolefins is developed by employing DDQ as the organophotoredox catalyst in combination with tert-BuONO (TBN) as a nitrating agent under visible-light irradiation. This green transition metal-free approach utilizes aerial oxygen as the terminal oxidant and occurs at room temperature. Following the established protocol, 41 different olefines containing broad diversity of substituents were nitrated in good to excellent yields. Mechanistic experiments and photophysical studies revealed the probable mechanism.

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Section: Methodsmentioning

confidence: 99%

Organophotoredox Catalyzed Stereoselective Nitration of Olefins with tert‐Butyl Nitrite under Air

et al. 2021

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2‐Methoxyethyl Nitrite as a Reagent for Chemoselective On‐Water Nitration

Kitanosono

Hashidoko

Yamashita

et al. 2022

Chemistry An Asian Journal

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An on-water approach has been developed that allows a nitration of tyrosines and phenols under mild conditions. We envisioned that the assembly of tyrosine/ tyrosyl radical couples with interfacial water molecules would realize a biomimetic stacking hydrogen atom transfer (HAT) transition state to facilitate the electron-transfer process. The optimal organic nitrite, 2-methoxyethyl nitrite, resulted in rapid coupling of the tyrosyl radicals with * NO 2 at the oilwater interface to afford the nitrated phenols. Many characteristics found in our on-water strategy are distinct from other complementary systems that include radical nitration. These enticing roles of water in the reaction process introduce new avenues to explore in the design of synthetic organic chemistry systems.

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Enantio- and Diastereoselective Michael Addition of Cyclic Ketones/Aldehydes to Nitroolefins in Water as Catalyzed by Proline-Derived Bifunctional Organocatalysts

2022

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New l-proline-derived bifunctional secondary amine organocatalysts were synthesized for enantioselective Michael reactions in water as a solvent. Application of these catalysts in Michael additions provided high yield (up to 97%) with high stereoselectivity (dr up to 99:1 and ee up to 99%). The effect of phenyl group at (R)-C6 in the catalyst was investigated and played a key role in successful catalysis by density functional theory computational calculations. The synthetic utility of this reaction was demonstrated by the formal synthesis of Sch 50971, which is a novel histamine H3 receptor agonist.

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Metal‐free Synthesis of β‐Nitrostyrenes via DDQ‐Catalyzed Nitration

Cited by 6 publications

References 38 publications

Organophotoredox Catalyzed Stereoselective Nitration of Olefins with tert‐Butyl Nitrite under Air

Organophotoredox Catalyzed Stereoselective Nitration of Olefins with tert‐Butyl Nitrite under Air

2‐Methoxyethyl Nitrite as a Reagent for Chemoselective On‐Water Nitration

Enantio- and Diastereoselective Michael Addition of Cyclic Ketones/Aldehydes to Nitroolefins in Water as Catalyzed by Proline-Derived Bifunctional Organocatalysts

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