Pd-catalyzed intermolecular consecutive double Heck reaction “on water” under air: facile synthesis of substituted indenes

Wei, Dong; Lu, Han-Yu; Miao, Han-Zhe; Feng, Chen‐Guo; Lin, Guo‐Qiang; Liu, Yingbin

doi:10.1039/d3ra03510g

Cited by 4 publications

(1 citation statement)

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“…The relevant studies on multi‐step Mizoroki‐Heck reactions involving the “on‐water” mechanism have shown promising outcomes as well. Very recently, Liu and colleagues [ 47 ] disclosed an intermolecular consecutive double Mizoroki‐Heck reaction…”

Section: Mizoroki‐heck−type Reactionsmentioning

confidence: 99%

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism^†

Wei,

Lin

2024

Chin. J. Chem.

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Comprehensive SummaryAs the chemical industry grapples with the need for more eco‐friendly practices, the use of water as a reaction medium is gaining traction in organic transformations. This mini‐review delves into Pd‐catalyzed reactions that utilize the "on‐water" mechanism, spanning from 2019 to late 2023. These reactions are neatly categorized into several types: (A) Catalytic C—H activations, (B) Mizoroki‐Heck‐type reactions, (C) Suzuki‐Miyaura reactions, and (D) Cyclization reactions. By showcasing the potential of water as a sustainable reaction medium for organic transformations, these reactions leave no doubt about the importance of embracing eco‐friendly practices in the chemical industry.This article is protected by copyright. All rights reserved.

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Section: Mizoroki‐heck−type Reactionsmentioning

confidence: 99%

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism^†

Wei,

Lin

2024

Chin. J. Chem.

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Iron-Catalyzed 5-Endo-Dig Synthetic Approach to Indenes and Its Bidirectional Extension to Narrow Bandgap π-Systems

Chen,

Itabashi,

Fukuma

et al. 2024

ACS Catal.

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The indene skeleton is a key structure in a variety of compounds, with applications in medicinal and materials science. Traditional syntheses often require harsh conditions or reactive intermediates due to the temporary disruption of the aromaticity of the developing indene ring. To circumvent this problem, we have investigated iron-catalyzed 5-endo-dig cyclization for the construction of the fivemembered carbocycle component of indene, which does not interrupt the benzene ring's aromaticity. A reduced iron reactive species generated by the reduction of FeCl 2 with metallic magnesium is a key reactive species that effectively cleaves the C−O bond in the starting material to generate a dormant radical-stabilized iron, which smoothly undergoes the 5-endo-dig closure of an indene ring. The synthetic conditions are so mild that we synthesized a high highest occupied molecular orbital (HOMO), narrow bandgap conjugated compound that has a HOMO level as high as −4.59 eV and an optical bandgap of 1.50 eV; hence, it is unstable even under air.

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Palladium nanoparticle catalyzed synthesis of indoles via intramolecular Heck cyclisation

Sarmah,

Choudhury,

Bora

2024

Org. Biomol. Chem.

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Pd-catalyzed intermolecular consecutive double Heck reaction “on water” under air: facile synthesis of substituted indenes

Abstract: An efficient and environmentally benign method for the preparation of substituted indenes has been developed by using water as the sole solvent.

Cited by 4 publications

References 49 publications

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism^†

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism^†

Iron-Catalyzed 5-Endo-Dig Synthetic Approach to Indenes and Its Bidirectional Extension to Narrow Bandgap π-Systems

Palladium nanoparticle catalyzed synthesis of indoles via intramolecular Heck cyclisation

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Pd-catalyzed intermolecular consecutive double Heck reaction “on water” under air: facile synthesis of substituted indenes

Abstract: An efficient and environmentally benign method for the preparation of substituted indenes has been developed by using water as the sole solvent.

Cited by 4 publications

References 49 publications

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism†

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism†

Iron-Catalyzed 5-Endo-Dig Synthetic Approach to Indenes and Its Bidirectional Extension to Narrow Bandgap π-Systems

Palladium nanoparticle catalyzed synthesis of indoles via intramolecular Heck cyclisation

Contact Info

Product

Resources

About

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism^†

Recent Advances in Pd‐Catalyzed Reactions Involving the “On‐Water” Mechanism^†