Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 109683 - 109683

Published: March 2, 2024

Language: Английский

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Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(20), P. 11435 - 11522

Published: Oct. 9, 2024

Arynes hold significance for the efficient fusion of (hetero) arenes with diverse substrates, advancing construction complex molecular frameworks. Employing multiple equivalents arynes is particularly effective in rapid formation polycyclic cores found optoelectronic materials and bioactive compounds. However, inherent reactivity often leads to side reactions, yielding unanticipated products underlining importance a detailed investigation into use fine-tune their reactivity. This review centers on methodologies syntheses organic reactions involving arynes, categorizing based mechanisms like cycloadditions, σ-bond insertions, nucleophilic additions, ene discusses aryne polymerization. The categorization these includes two primary approaches: first entails engagement within single step while second approach involves using equivalent sequentially across steps, both requiring strict control ensure precise participation each respective step. Additionally, provides an in-depth analysis selection precursors, organized chronologically by activation strategy, offering comprehensive background that supports main theme utilization. expectation remains this will be invaluable designing advanced engaging arynes.

Language: Английский

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Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3670 - 3675

Published: July 2, 2024

Abstract With an in situ C−H iodination tactic, a method for the synthesis of chromone‐3‐phosphonates was developed with trialkyl/triaryl phosphites as reaction partners o ‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists cascade iodination, chromone annulation, and Arbuzov‐type C−P cross coupling major transformations. In addition to providing enaminone‐based synthetic chromone‐3‐phosphonates, work shows advantage step economy skipping separate operation preparing iodo‐functionalized intermediate.

Language: Английский

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Palladium-catalyzed decarboxylation [2 + 2 + 2] annulation approach to chromone-containing polycyclic compounds

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3752 - 3759

Published: Jan. 1, 2023

A variety of chromone-containing polycyclic compounds are efficiently generated via Pd-catalyzed decarboxylation [2 + 2 2] annulation 3-iodochromones, bridged olefins and o-bromobenzoic acids, in which o -bromobenzoic acids were employed as the electrophilic aryl units.

Language: Английский

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Practical Access to Fused Carbazoles via Oxidative Benzannulation and their Photophysical Properties

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9586 - 9596

Published: June 20, 2024

An aryne annulation strategy for the synthesis of fused carbazoles is developed using indolyl β-ketonitrile in a cascade manner. The reaction sequence involves aryne-mediated [2 + 2] cycloaddition cleavage and intramolecular Michael addition, followed by oxidation under transition-metal-free conditions. Subsequently, conversion benzo[b]carbazole-6-carbonitrile to carbazole quinone observed upon prolongation time. Furthermore, these materials exhibit high quantum efficiency, which promotes light-emitting diode applications.

Language: Английский

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Easy Access to Phenanthridinones via Metal-Free Cascade Benzannulation and C–N Bond Formation

Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8408 - 8412

Published: Nov. 16, 2023

A concise route for the synthesis of dihydrobenzo[j]phenanthridinones has been disclosed through an aryne annulation strategy under metal-free reaction conditions. The involves multiple C-C and C-N bond cleavages/formations via Diels-Alder reaction, aromatization-driven cleavage, amide formation.

Language: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 421 - 484

Published: Jan. 1, 2024

Language: Английский

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