Synthesis and Halochromic Properties of 1,2,6‐Tri‐ and 1,2,3,6‐Tetra‐aryl Azulenes DOI
Qiang Zhu, Zhuang Mao Png, Tingting Lin

et al.

ChemPlusChem, Journal Year: 2021, Volume and Issue: 86(8), P. 1116 - 1122

Published: July 27, 2021

Abstract A series of novel 2,6‐functionalized azulene molecules Azu1‐3 with varied fluorene substituents at the 1‐ and 3‐positions as well 5’‐position 2‐thiophene group were synthesized. Their electronic absorption emission spectra neutral protonated states examined. It was found that after functionalization fluorenyl groups, exhibited maxima 445, 451 to 468 nm, respectively. In contrast, their corresponding species showed much redshifted 560, 582 643 respectively, mainly due extension conjugation length large dipole moment along C 2v axis 2,6‐substituted molecules. are non‐fluorescent in forms, but became emissive states. Analysis shows substitution or 3‐position led decrease response trifluoroacetic acid.

Language: Английский

Ruthenium(ii)-catalyzed synthesis of CF3-isoquinolinones via C–H activation/annulation of benzoic acids and CF3-imidoyl sulfoxonium ylides DOI

Si Wen,

Yu‐Qing Zhang,

Qingyu Tian

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(16), P. 4388 - 4393

Published: Jan. 1, 2022

The synthesis of 3-trifluoromethylisoquinolinones by a ruthenium( ii )-catalyzed C–H activation/annulation reaction benzoic acids and CF 3 -imidoyl sulfoxonium ylides has been achieved.

Language: Английский

Citations

42
Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides DOI

Pratiksha Bhorali,

Sabera Sultana, Sanjib Gogoi

et al.

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

Citations

41
Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine DOI
Luyao Liu,

Jingyang Lin,

Mingxuan Pang

et al.

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

Citations

29
Metal-free cascade O–H double insertion between I(III)/S(VI)-ylides, carboxylic acids, and alcohols: modular access to unsymmetrical α,α-O,O-substituted ketones DOI

Jiaohang Wei,

Wen‐Xuan Zou,

Qiong Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3234 - 3241

Published: Jan. 1, 2024

Herein, we present a cascade O–H double insertion reaction between I (III) /S (VI) -ylides, carboxylic acids, and alcohols under metal-free conditions, enabling the modular synthesis of unsymmetrical α,α- O , -substituted ketones.

Language: Английский

Citations

8
Annulation of CF3–Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles DOI

Si Wen,

Qingyu Tian,

Yanhui Chen

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(19), P. 7407 - 7411

Published: Sept. 20, 2021

A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have obtained in 27–78% yield. This features a broad substrate scope generates dimethyl sulfoxide H2O as byproducts.

Language: Английский

Citations

40
Iridium(III)-Catalyzed B(4)-Acylmethylation and B(3,5)-Diacylmethylation from o-Carboranes and Sulfoxonium Ylides DOI
Gi Hoon Ko, Kyusik Um, Hee Chan Noh

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(8), P. 1604 - 1609

Published: Feb. 17, 2022

An iridium(III)-catalyzed regioselective acylmethylation of the cage B(4)-H bond in o-carborane acids with sulfoxonium ylides is demonstrated through activation ethanol under very mild conditions, affording a number B(4)-acylmethylated o-carboranes. Additionally, selective sequential B(4)- and B(6)-acylmethylation reactions finally gave B(3,5)-diacylmethylated o-carboranes one pot.

Language: Английский

Citations

22
α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group DOI
Anurag Singh, Shreemoyee Kumar, Chandra M. R. Volla

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(5), P. 879 - 909

Published: Dec. 6, 2022

Transition metal-catalyzed cross-coupling of sp2 C-H bonds with diazo compounds via carbene migratory insertion represents an efficient strategy for the construction C-C and C-heteroatom in organic synthesis. Despite popularity as coupling partners activation, they pose serious safety stability issues due to potential exothermic reactions linked release N2 gas. However, compared compounds, sulfoxonium ylides are generally crystalline solids, more stable, widely used industrial scales, easier/safer prepare. Therefore, recent years have witnessed upsurge employing α-carbonyl alternative surrogate transition activation. Unlike contain inherent serve a partner well weak directing group. This review will summarize progress made both categories reactions.

Language: Английский

Citations

21
Synthesis of Pyrazolo[1,2‐a]cinnolines via Rhodium(III)‐Catalyzed [4+2] Annulation Reactions of Pyrazolidinones with Sulfoxonium Ylides DOI

Shulei Hu,

Xu Han,

Xiong Xie

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(13), P. 3311 - 3317

Published: May 8, 2021

Abstract A method to synthesize pyrazolo[1,2‐a]cinnolines via rhodium(III)‐catalyzed C−H activation of pyrazolidinones and subsequent [4+2] annulation sulfoxonium ylides was developed. 5‐Substituted or 5,10‐disubstituted could be obtained by slightly adjusting the reaction conditions. Gram‐scale synthesis practical transformations proved practicability this method. The mechanism proposed in article on basis preliminary mechanistic results previous reports. This features simplified operation, metal‐oxidant free, readily available reactants. magnified image

Language: Английский

Citations

25
Hydroxyl-Directed Ruthenium-Catalyzed peri-Selective C–H Acylmethylation and Annulation of Naphthols with Sulfoxonium Ylides DOI
Wenbo Ma,

Yuqiang Tan,

Yang Wang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6200 - 6205

Published: Aug. 2, 2021

Herein, we report a highly efficient ruthenium-catalyzed peri-selective C(sp2)–H acylmethylation of 1-naphthols with α-carbonyl sulfoxonium ylides by utilizing hydroxyl as weakly coordinating directing group. This new method imparts good reactivity, excellent chemo- and regioselectivity, broad functional group tolerance involves mild reaction conditions. The C–H acylmethylated products can be readily cyclized into fluorescent annulated pyrans one-pot process.

Language: Английский

Citations

25
New trends in the synthesis of azulene-fused heterocycles DOI
Ahmed H. M. Elwahy, Mohamed R. Shaaban, Ismail A. Abdelhamid

et al.

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0