Research Progress of Sulfoxonium Ylides in the Construction of Five/Six-Membered Nitrogen-Containing Heterocycles DOI
Jiantao Zhang, Cong Zhang,

Zidong Zheng

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(9), P. 2745 - 2745

Published: Jan. 1, 2022

Language: Английский

HFIP in Organic Synthesis DOI
Hashim F. Motiwala,

Ahlam M. Armaly,

Jackson G. Cacioppo

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(15), P. 12544 - 12747

Published: July 17, 2022

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.

Language: Английский

Citations

319
Application of sulfoxonium ylide in transition-metal-catalyzed C-H bond activation and functionalization reactions DOI
Anil Kumar, Mahadev Sharanappa Sherikar, Vinayak Hanchate

et al.

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

Published: Oct. 8, 2021

Language: Английский

Citations

71
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
Transition-Metal-, Additive-, and Solvent-Free [3 + 3] Annulation of RCF2-Imidoyl Sulfoxonium Ylides with Cyclopropenones to Give Multifunctionalized CF3-Pyridones DOI

Si Wen,

Yanhui Chen,

Qingyu Tian

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 87(2), P. 1124 - 1132

Published: Dec. 29, 2021

An efficient and practical strategy was developed to synthesize 1,3,4-triaryl-6-trifluoromethylpyridones from CF3-imidoyl sulfoxonium ylides cyclopropenones in good excellent yields. This stepwise [3 + 3] annulation reaction carried out under transition-metal-, additive-, solvent-free conditions, generating 1 equiv of dimethyl sulfoxide as byproduct tolerating a series functional groups.

Language: Английский

Citations

42
Metal-Free Syntheses of α-Ketothioamide and α-Ketoamide Derivatives from Sulfoxonium Ylides DOI

Trayambek Nath Chaubey,

Paran J. Borpatra, Ajay Sharma

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(43), P. 8062 - 8066

Published: Oct. 24, 2022

An efficient base, additive and metal-free synthetic methods for α-ketothioamide α-ketoamide derivatives from readily available sulfoxonium ylides have been described. Sulfoxonium with primary or secondary amines afforded α-ketothioamides in the presence of elemental sulfur, whereas α-ketoamides were produced when I2 TBHP present. The reaction proceeded well at room temperature generated corresponding molecules good to excellent yields. can be scaled-up tolerated by a range functional groups simple operational procedures.

Language: Английский

Citations

37
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
Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones with iodonium ylides to give substituted isocoumarins DOI

Mingshuai Zhang,

Longkun Chen,

Donghan Liu

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(26), P. 12274 - 12278

Published: Jan. 1, 2023

A wide variety of isocoumarin derivatives are easily constructed via a Rh( iii )-catalyzed C–H bond activation/annulation cascade reaction.

Language: Английский

Citations

14
Substituted Isocoumarins: An Assemble of Synthetic Strategies Towards 3‐Substituted and 3,4‐Disubstituted Isocoumarins DOI

Kangkana Chutia,

Manashi Sarmah, Pranjal Gogoi

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(5)

Published: Jan. 17, 2023

The versatility of isocoumarin frameworks offers the privilege to access many pharmacological targets. This unique heterocycle core present in natural products and complex organic molecules contribute medicinal chemistry as anti-cancer, anti-inflammatory immunomodulatory agents. attractive properties exhibited by its analogues urged scientists explore their synthetic analogues. In regard myriads methodologies, we have compiled a review update covering all articles that been published towards synthesis 3-substituted 3,4-disubstituted isocoumarins. Additionally, also highlighted systematic survey catalytic methods for along with scope diverse functionalizations plausible mechanistic aspects.

Language: Английский

Citations

13
Catalytic Asymmetric C–H Activation/Cyclization of Sulfoximines with Sulfoxonium Ylides by a Chiral η6-Benzene Ruthenium(II) Catalyst DOI
Huan Liu, Ji‐Jun Jiang, Jun Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 17398 - 17404

Published: Nov. 12, 2024

Chiral η6-benzene ruthenium(II) (BenRuII)-catalyzed asymmetric C–H activations are challenging and rarely seen in the literature. Herein, activation/cyclization of sulfoximines with sulfoxonium ylides catalyzed by chiral BenRuII catalyst derived from (S)-H8–BINOL is described. It provides efficient access to various sulfur-chiral 1,2-benzothiazine 1-oxides high yields enantioselectivities (up 99% yield 98% ee). Kinetic resolution racemic was also feasible. The reaction mechanism studied tool H/D exchange kinetic isotope effect. metallacycle revealing origin induction prepared, characterized, proved effective for model reaction. This work demonstrates great potential catalysts activation.

Language: Английский

Citations

5