Recent advances in visible light-mediated chemical transformations of enaminones

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

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Condition-Controlled Selective Synthesis of Pyranone-Tethered Indazoles or Carbazoles through the Cascade Reactions of N-Nitrosoanilines with Iodonium Ylides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(24), P. 4422 - 4428

Published: June 8, 2023

Presented herein is a condition-controlled selective synthesis of pyranone-tethered indazoles or carbazole derivatives via the cascade reactions N-nitrosoanilines with iodonium ylides. Mechanistically, formation former involves an unprecedented process including nitroso group-directed C(sp2)–H bond alkylation N-nitrosoaniline ylide followed by intramolecular C-nucleophilic addition to moiety, solvent-assisted cyclohexanedione ring opening, and transesterification/annulation. On contrary, latter initial annulation denitrosation. These developed protocols feature easily controllable selectivity, mild reaction conditions, clean sustainable oxidant (air), valuable products that are structurally diverse. In addition, utility was showcased their facile diverse transformations into synthetically biologically interesting compounds.

Language: Английский

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Rh-Catalyzed and Self-Directed Aromatic C–H Activation of Enaminones to Divergent Alkenylated and Annulated Compounds

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

By means of simple Rh catalysis, the direct activation ortho-C-H bond in aryl enaminones has been realized with enaminone structure as a traceless directing fragment. The products resulting from C-H alkenylation and further annulation via intramolecular addition could be accessed depending upon alkenes. annulated used for easy synthesis valuable 2-aza-fluorenones one-pot operation by employing NH4OAc.

Language: Английский

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Catalytic C H activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109494 - 109494

Published: Jan. 6, 2024

Language: Английский

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Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1744 - 1750

Published: Feb. 22, 2024

Abstract The transmetalation triggered rhodium‐catalyzed C−H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium has been developed. Various products phenanthrenes were constructed under redox‐neutral conditions in 34–86% yields. Several mechanism exploration experiments derivatization reactions conducted sequence to gain a deeper understanding the process potential this transformation. It offers an alternative approach for synthesis phenanthrene derivatives.

Language: Английский

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Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Language: Английский

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Enaminone-directed ruthenium(ii)-catalyzed C–H activation and annulation of arenes with diazonaphthoquinones for polycyclic benzocoumarins

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(88), P. 13187 - 13190

Published: Jan. 1, 2023

Weakly coordinating enaminone functionality has been leveraged for C–H activation strategy under ruthenium catalysis the regioselective annulative coupling of arenes with diazonaphthoquinones, offering polycyclic benzocoumarins in high yields.

Language: Английский

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Photocatalytic Three-Component Assemblies of Enaminones, α-Diazo Esters, and Nitriles for the Synthesis of N,N-Diacylated Glycine Esters

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 21, 2025

A facile method with simple starting materials, including enaminones, α-diazo esters, and nitriles, has been developed for the direct synthesis of N,N-diacyl glycine esters via visible light photocatalysis. The reaction involves a novel carbon-carbon bond cleavage in leading to products high tolerance variability substructures among all three components.

Language: Английский

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