Photochemical Aryl Radical Cyclizations to  Give (E)-3-Ylideneoxindoles

Gurry, Michael; Allart‐Simon, Ingrid; McArdle, Patrick; Gérard, Stéphane; Sápi, János; Aldabbagh, Fawaz

doi:10.3390/molecules191015891

Cited by 3 publications

(1 citation statement)

References 24 publications

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“…In the last two decades increased attention was focused on light-induced chemical transformations, especially in the field of radical chemistry [18,19]. UV or visible light can be used as green, sustainable and inexpensive sources of energy.…”

Section: Sp 3 C-centered Radical-promoted Rearrangementsmentioning

confidence: 99%

Radical Smiles Rearrangement: An Update

2016

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Over the decades the Smiles rearrangement and its variants have become essential synthetic tools in modern synthetic organic chemistry. In this mini-review we summarized some very recent results of the radical version of these rearrangements. The selected examples illustrate the synthetic power of this approach, especially if it is incorporated into a domino process, for the preparation of polyfunctionalized complex molecules.

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Section: Sp 3 C-centered Radical-promoted Rearrangementsmentioning

confidence: 99%

Radical Smiles Rearrangement: An Update

2016

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Divergent and Selective Synthesis of 3-Alkylidene Oxindoles Using Pd-Catalyzed Multicomponent Reaction

2023

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Herein, a divergent and selective synthesis of (E)-3alkylidene oxindole, which is a highly valuable framework due to its presence in biologically important molecules, via palladiumcatalyzed multicomponent reaction of 3-diazo oxindole, isocyanide, and aniline has been developed. Further, the feasibility of the reaction was demonstrated by employing differently substituted 3diazo oxindoles, isocyanides, and anilines as starting material and obtaining the corresponding products in 31−83% isolated yields. Besides, a plausible mechanism has been presented and further investigated using DFT calculations which suggest the formation of the Pd-carbene complex and ketenimine intermediate as the key step during the catalytic cycle.

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Tris(trimethylsilyl)silane and visible-light irradiation: a new metal- and additive-free photochemical process for the synthesis of indoles and oxindoles

et al. 2015

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A combined tris(trimethylsilyl)silane and visible-light-promoted intramolecular reductive cyclization protocol for the synthesis of indoles and oxindoles has been developed. This straightforward and efficient method shows tolerance towards a broad spectrum of functional-groups and enables rapid and practical synthesis of functionalized nitrogen-based heterocycles in high yields under additive and metal-free, mild photochemical conditions.

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Photochemical Aryl Radical Cyclizations to Give (E)-3-Ylideneoxindoles

Cited by 3 publications

References 24 publications

Radical Smiles Rearrangement: An Update

Radical Smiles Rearrangement: An Update

Divergent and Selective Synthesis of 3-Alkylidene Oxindoles Using Pd-Catalyzed Multicomponent Reaction

Tris(trimethylsilyl)silane and visible-light irradiation: a new metal- and additive-free photochemical process for the synthesis of indoles and oxindoles

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