Visible light-induced synthesis of (<i>Z</i>)-β-iodoenamides from <i>N</i>-vinyl amides mediated by the ion pair charge transfer state

Sun, Rui; Yang, Xiao; Ge, Yicen; Zheng, Xueli; Li, Ruixiang; Fu, Haiyan; Chen, Hua

doi:10.1039/d2qo00050d

Cited by 5 publications

(2 citation statements)

References 51 publications

(26 reference statements)

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“…According to the above results and related reports, a plausible mechanism of the hydroalkoxylation of enamides catalyzed by N -heteroarenium iodides was proposed (Scheme ). First, the contact ion pair of PI-9 was formed in 1,4-dioxane, which interacted with enamide 1a via a weak coordination.…”

Section: Resultsmentioning

confidence: 99%

“…N -Heteroarenium iodides, owing to the easily available and modulated character, have exhibited exceptionally rich chemistry in organic synthesis and have been applied as a photosensitizer in photoredox catalytic reactions, but its function as a catalyst in the hydrofunctionalization of olefins has not yet been explored. Herein, we report the first N -heteroarenium iodide-catalyzed hydroalkoxylation of enamides with alcohols or thioalcohols to synthesize N,O- or N,S-acetals (Scheme B).…”

Section: Introductionmentioning

confidence: 99%

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Hydroalkoxylation of Enamides Catalyzed by N-Heteroarenium Iodides

Sun,

Wang,

Liang

et al. 2024

J. Org. Chem.

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A facile and novel N-heteroarenium iodide-catalyzed hydroalkoxylation of enamides has been described. The protocol provides easy access to N,O-acetals, which proved to be a versatile synthetic synthon. The hydrosulfonylation, hydroamination, and hydrophosphorylation products of enamide could be indirectly provided from N,O-acetals. The reaction mechanism was further investigated, which indicated that the hydroalkoxylation of enamides was driven by weak coordination between enamide and the contact ion pair of N-heteroarenium iodide.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hydroalkoxylation of Enamides Catalyzed by N-Heteroarenium Iodides

Sun,

Wang,

Liang

et al. 2024

J. Org. Chem.

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Iodine‐Mediated Regioselective Radical Cyclization of o‐Vinylaryl Isocyanides with Disulfides/Diselenides Leading to 2‐Chalcogenated Quinolines

Li,

Chen,

Zhang

et al. 2023

Adv Synth Catal

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Catalytic Strategies for the Selective Synthesis of α‐ and β‐Functionalized Amines via Hydrofunctionalization of Enamides

Sun,

Yang

2024

Adv Synth Catal

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α‐ and β‐functionalized amines are two classes of important compounds, whose structural units are widely present in approved drugs. The hydrofunctionalization of enamides is the most direct and efficient method for constructing these two types of compounds. The regioselectivity was the focus of this conversion, which is largely influenced by the catalytic mode. Therefore, in order to selectively synthesize α‐ or β‐functionalized amines, the progress in catalytic hydrofunctionalization of enamides over the past decade are reviewed, and the catalytic pathways for the hydrofunctionalization of enamides are discussed in detail. This account aims to objectively evaluate the effects of various catalytic pathways on the regioselectivity of hydrofunctionalization, in order to provide a new perspective on the selection of catalytic methods and the design of catalytic pathways for selective synthesis α‐ or β‐functionalized amines. This review has been divided into the following sections: 1. Introduction 2. Organic reagents catalysis 3. Transition metal catalysis 4. Photoredox catalysis 5. Summary and prospect Keywords: α‐ and β‐functionalized amines; enamides; regioselectivity; hydrofunctionalization; catalytic strategies

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Visible light-induced synthesis of (Z)-β-iodoenamides from N-vinyl amides mediated by the ion pair charge transfer state

Abstract: A facile and novel approach for high chemo- and stereoselective synthesis of (Z)-β-iodoenamides from N-vinyl amides has been developed based on a visible-light-induced ion pair charge transfer state derived from...

Cited by 5 publications

References 51 publications

Hydroalkoxylation of Enamides Catalyzed by N-Heteroarenium Iodides

Hydroalkoxylation of Enamides Catalyzed by N-Heteroarenium Iodides

Iodine‐Mediated Regioselective Radical Cyclization of o‐Vinylaryl Isocyanides with Disulfides/Diselenides Leading to 2‐Chalcogenated Quinolines

Catalytic Strategies for the Selective Synthesis of α‐ and β‐Functionalized Amines via Hydrofunctionalization of Enamides

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