Ru^II-Catalyzed/NH₂-Assisted Selective Alkenyl C–H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines

Organic Letters, Journal Year: 2019, Volume and Issue: 21(12), P. 4812 - 4815

Published: June 13, 2019

A novel ruthenium-catalyzed [5 + 1] annulation of 2-alkenylanilines with sulfoxonium ylides was developed for the rapid assembly highly functionalized quinolines. This new catalytic process employs challenging but synthetically ideal free amino functionality to achieve alkenyl C–H activation as one-carbon coupling partners. Various 2-acylquinolines could be obtained good yields and excellent functional group tolerance. Moreover, potential synthetic application this methodology exemplified by several chemical transformations.

Language: Английский

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Synthesis of indoles and quinazolines via additive-controlled selective C–H activation/annulation of N-arylamidines and sulfoxonium ylides

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(28), P. 4039 - 4042

Published: Jan. 1, 2019

Selective synthesis of indoles and quinazolines was achieved through a precise control C–H activation/annulation by changing additives.

Language: Английский

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Rhodium-Catalyzed Reaction of Sulfoxonium Ylides and Anthranils toward Indoloindolones via a (4 + 1) Annulation

Organic Letters, Journal Year: 2019, Volume and Issue: 21(17), P. 6653 - 6657

Published: Aug. 19, 2019

A rhodium-catalyzed annulation between aroyl sulfoxonium ylides and anthranils has been developed to synthesize 10H-indolo[1,2-a]indol-10-one derivatives. This reaction started with an unpredented (4 + 1) toward N-(2-formylphenyl) indolones, proceeding the sequential ortho-amination of C–H bond in by insertion N–H carbene. Finally, Aldol condensation constructed second indole ring. procedure features formation two C–N bonds one C═C pot.

Language: Английский

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Application of sulfoxonium ylide in transition-metal-catalyzed C-H bond activation and functionalization reactions

Tetrahedron, Journal Year: 2021, Volume and Issue: 101, P. 132478 - 132478

Published: Oct. 8, 2021

Language: Английский

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Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(4)

Published: March 23, 2022

Abstract In recent years, the transition‐metal‐catalyzed functionalization reactions of sulfoxonium ylides have been explored extensively because their usefulness as carbene‐transfer agents, since they can produce metal carbenes through catalysis. Moreover, are safer and advantages simple handling good stability over other counterparts like diazo‐compounds. This review article attempts to highlight advances in metal‐catalyzed C−H ylides.

Language: Английский

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Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides

Organic Letters, Journal Year: 2020, Volume and Issue: 22(4), P. 1504 - 1509

Published: Feb. 11, 2020

An unprecedented copper-catalyzed reaction of sulfoxonium ylides and anthranils is reported that enables an easy access to 2,3-diaroylquinolines through a [4+1+1] annulation. Copper-catalyzed homocoupling provided α,α,β-tricarbonyl ylides, which provides strategy extend the carbon chain C–C bond formation. The utility products as well mechanistic details process are presented.

Language: Английский

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Rhodium(III)-Catalyzed Regioselective C3–H Acylmethylation of [2,2′-Bipyridine]-6-carboxamides with Sulfoxonium Ylides

Organic Letters, Journal Year: 2019, Volume and Issue: 21(16), P. 6366 - 6369

Published: July 30, 2019

A rhodium(III)-catalyzed C–H acylmethylation of tridentate [2,2′-bipyridine]-6-carboxamides was developed. variety could be monoalkylated exclusively at the C3 position with sulfoxonium ylides as carbene precursors, giving 3-alkylated products in high yields. This protocol proceeds through a rollover cyclometalation pathway, has broad range scope substrates, and exhibits excellent functional group tolerance.

Language: Английский

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Rh(III)-Catalyzed Reaction of α-Carbonyl Sulfoxonium Ylides and Alkenes: Synthesis of Indanones via [4 + 1] Cycloaddition

Organic Letters, Journal Year: 2020, Volume and Issue: 22(4), P. 1375 - 1379

Published: Feb. 3, 2020

The synthesis of indanone derivatives by the Rh(III)-catalyzed reaction α-carbonyl sulfoxonium ylides with activated alkenes is reported. shows a high tolerance for functional groups and furnishes variety substituted via formal [4 + 1] cycloaddition. Highly stable were used as substrates in this C-H functionalization, their bifunctional character could be effectively exploited using Rh(III) catalysis sequential double C-C bond formation. Based on mechanistic studies including deuterium-labeling experiments, proposed to proceed follows: oxidative alkenylation β-hydride elimination, readdition H-Rh species, 1,2-carbon shift elimination DMSO, protonation.

Language: Английский

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Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine

Organic Letters, Journal Year: 2022, Volume and Issue: 24(5), P. 1146 - 1151

Published: Feb. 3, 2022

A novel photo-thermo-mechanochemical approach to assembling quinolines catalyzed by iron(II) phthalocyanine has been realized for the first time. This transformation features a cost-efficient catalytic system and operational simplicity, is free of solvent, shows good substrate tolerance, providing green alternative existing thermal approaches. Mechanistic experiments demonstrate that in-situ-formed secondary amine may be key intermediate further cyclization/aromatization process.

Language: Английский

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Synthesis of Furoxans and Isoxazoles via Divergent [2 + 1 + 1 + 1] Annulations of Sulfoxonium Ylides and ^tBuONO

Organic Letters, Journal Year: 2019, Volume and Issue: 21(13), P. 5273 - 5276

Published: June 26, 2019

We have presented a simple and new method for the divergent assembly of furoxans isoxazoles in which [2 + 1 1] annulation reaction sulfoxonium ylides is reported first time. When was performed using tBuONO as nitrogen source without metal catalyst, desired were obtained decent yields with wide substrate scope. Isoxazoles bearing three carbonyl groups achieved when conducted Cu(TFA)2 catalyst.

Language: Английский

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