Unveiling a carbazole-based photocatalyst for visible-light-driven synthesis of indolyl diarylmethanes and 2-benzimidazoles

Catalysis Science & Technology, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A carbazole-based photocatalyst (MD) incorporating a dicyanovinyl acceptor and exhibiting superior redox potential has been demonstrated for sustainable photocatalytic approach to synthesize indolyl diarylmethanes 2-substituted benzimidazoles.

Язык: Английский

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Conjugated 1,8 and 1,6 Addition of Bis-Trimethylsilylketene Acetal to Activated p-Quinone Methides via Trifluoromethanesulfonic Anhydride

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 31, 2025

In this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to para-quinone methides (p-QMs), which are one most explored molecules for study and gained significant attention in organic chemistry due their versatile reactivity, particularly Michael addition reactions. study, trifluoromethanesulfonic anhydride (Tf2O) was used as an activating agent p-QMs, aiming achieve 1,6-Michael products least reported 1,8-Michael with pyridine substituents. The reactivity p-QMs derived from demonstrated distinct reaction pathways, leading formation δ γ lactones. investigation also involved synthesizing a 1-indanone carboxylic acids obtained 1,6-addition.

Язык: Английский

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Electrochemical benzylic deuteration of p-QMs enabling the synthesis of benzylic deuterated diarylmethanes

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(20), С. 4047 - 4051

Опубликована: Янв. 1, 2024

Herein, electroreductive umpolung benzylic deuteration of p -QMs using cheap and easily accessible D 2 O as a deuterium source is reported.

Язык: Английский

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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

Chemistry - An Asian Journal, Год журнала: 2023, Номер 19(4)

Опубликована: Дек. 22, 2023

Abstract We devised a palladium‐catalyzed α ‐stereoselective glycosylation that incorporates oxygen via in‐situ generation of gem ‐disubstituted methanols from p ‐quinone methides to access 2,3‐unsaturated ‐diarylmethyl O ‐glycosides under open‐air atmosphere at room temperature. Advantages this environmentally friendly strategy include the absence additives and ligands, using water as green source oxygen, mildest, operationally simple, exhibiting wide functional group tolerance, compatibility with variety glycal progenitors in appreciable yields. A mechanistic study has been verified H 2 18 labeling, which validates (moisture) is sole oxygen.

Язык: Английский

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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

ChemistrySelect, Год журнала: 2024, Номер 9(4)

Опубликована: Янв. 22, 2024

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

Язык: Английский

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Eosin Y‐catalyzed reductive homocoupling of para‐quinone methides under visible‐light

Photochemistry and Photobiology, Год журнала: 2024, Номер 100(4), С. 1078 - 1088

Опубликована: Апрель 10, 2024

Abstract In this manuscript, we demonstrate a visible‐light driven dimerization of para ‐quinone methides using eosin Y catalyst via reductive homocoupling process. This mild and operationally simple methodology was found to be compatible with variety differently substituted broad range tetra‐arylethane derivatives were obtained in moderate good yields (47%–87%).

Язык: Английский

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

ChemCatChem, Год журнала: 2024, Номер 16(23)

Опубликована: Авг. 22, 2024

Abstract The ability to change the essential characteristics of molecular systems using light is highly promising and finds use in photocatalysis materials chemistry. A critical requirement for such that molecules should directly absorb visible region. Though small molecule activation by challenging, they on complexation with certain species respond favourably. Herein, we disclose catalytic application CBr 4 as a halogen bond donor catalyst activate para ‐quinone methides towards photo‐catalysed reactions. This protocol facilitates 1,6‐conjugate addition reactions various nucleophiles, forming C−C C−O bonds methides, yielding desired products good excellent yields. Mechanistic investigations reveal para‐ quinone methide responds only when complexed . synthetic utility this demonstrated through one‐pot synthesis spiro‐cyclohexadienone compounds from 2‐naphthol methide.

Язык: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

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Silica mediated 1,6-conjugate addition of indoles and other heterocycles to p-quinone methides under solvent free condition

Tetrahedron Letters, Год журнала: 2024, Номер unknown, С. 155398 - 155398

Опубликована: Ноя. 1, 2024

Язык: Английский

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