Visible-light-mediated radical reactions of indoles with<i>para</i>-quinone methides using eosin Y as an organophotoredox catalyst

Rekha, Rekha; Sharma, Sonam; Anand, Ramasamy Vijaya

doi:10.1039/d3ob00852e

Cited by 8 publications

References 84 publications

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An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

Azeem,

Dubey,

Islam

et al. 2024

Chemistry An Asian Journal

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We devised a palladium‐catalyzed α‐stereoselective glycosylation that incorporates oxygen viain‐situ generation of gem‐disubstituted methanols from p‐quinone methides to access 2,3‐unsaturated gem‐diarylmethyl O‐glycosides under open‐air atmosphere at room temperature. Advantages of this environmentally friendly strategy include the absence of additives and ligands, using water as the green source of oxygen, mildest, operationally simple, exhibiting a wide functional group tolerance, and compatibility with a variety of glycal progenitors in appreciable yields. A mechanistic study has been verified via H218O labeling, which validates that water (moisture) is a sole source of oxygen.

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An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

Azeem,

Dubey,

Islam

et al. 2024

Chemistry An Asian Journal

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Halogen Bond Assisted Light Responsiveness of Para‐Quinone Methides for 1,6‐Conjugate Addition Reactions

Kumar,

Justin Thomas

2024

ChemCatChem

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The ability to change the essential characteristics of the molecular systems using light is highly promising and finds use in photocatalysis and materials chemistry. A critical requirement for such systems is that molecules should directly absorb light in the visible region. Though small molecule activation by visible light is challenging, they on complexation with certain species respond to visible light favourably. Herein, we disclose the catalytic application of CBr4 as a halogen bond donor catalyst to activate para‐quinone methides towards visible light photo‐catalysed reactions. This protocol facilitates 1,6‐conjugate addition reactions with various nucleophiles, forming C‐C and C‐O bonds in para‐quinone methides, yielding the desired products in good to excellent yields. Mechanistic investigations reveal that para‐quinone methide responds to visible light only when complexed with CBr4. The synthetic utility of this protocol is demonstrated through the one‐pot synthesis of spiro‐cyclohexadienone compounds from 2‐naphthol and para‐quinone methide.

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PTSA‐Mediated Bis 1,6‐Conjugate Addition of N‐Alkylcarbazoles and N‐Alkyliminodibenzyls to para‐Quinone Methides: Synthesis of Heterocyclic Bis Triarylmethanes

Sanjana,

Gurumurthy,

Parthasarathy

2024

ChemistrySelect

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An efficient and simple PTSA‐mediated bis 1,6‐conjugate addition of N‐alkylcarbazoles, N‐alkyliminodibenzyls and hydroquinone to para‐quinone methides is discussed. This protocol is useful to prepare various bis‐triarylmethanes in good to excellent yields under mild reaction conditions with good functional group tolerance. It is important to mention that, these heterocyclic triarylmethanes are often used in the biological community.

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Visible-light-mediated radical reactions of indoles withpara-quinone methides using eosin Y as an organophotoredox catalyst

Abstract: We demonstrate a redox-neutral, operationally simple, atom-economical, and additive-free approach for the synthesis of indolyl diarylmethanes via radical reactions of indoles with para-quinone methides (p-QMs) under visible-light mediated reaction conditions...

Cited by 8 publications

References 84 publications

An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

Halogen Bond Assisted Light Responsiveness of Para‐Quinone Methides for 1,6‐Conjugate Addition Reactions

PTSA‐Mediated Bis 1,6‐Conjugate Addition of N‐Alkylcarbazoles and N‐Alkyliminodibenzyls to para‐Quinone Methides: Synthesis of Heterocyclic Bis Triarylmethanes

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