Synthesis of Multifunctionalized Thiazolidine‐4‐thiones via [2+2+1] Annulation of Isothiocyanates and CF3‐Imidoyl Sulfoxonium Ylides DOI

Yuhao Ding,

Hailin Guo,

Jing-Wen Fan

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4672 - 4676

Опубликована: Ноя. 10, 2023

Abstract 2‐Iminothiazolidin‐4‐one, 5‐ethylidenethiazolidin‐4‐one, and thiazolidine‐4‐thione are all medicinally relevant structures. In this work, a NaSO 2 CF 3 ‐promoted [2+2+1] cascade annulation reaction of ‐imidoyl sulfoxonium ylides isothiocyanates was reported to synthesize variety decorated thiazolidine‐4‐thiones in 35–91% yields with exclusive stereoselectivity. The gram‐scale further chemoselective S ‐alkylations demonstrated the synthetic utilities transformation.

Язык: Английский

HFIP in Organic Synthesis DOI
Hashim F. Motiwala,

Ahlam M. Armaly,

Jackson G. Cacioppo

и другие.

Chemical Reviews, Год журнала: 2022, Номер 122(15), С. 12544 - 12747

Опубликована: Июль 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.

Язык: Английский

Процитировано

325

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

и другие.

Tetrahedron, Год журнала: 2021, Номер 101, С. 132478 - 132478

Опубликована: Окт. 8, 2021

Язык: Английский

Процитировано

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(16), С. 4388 - 4393

Опубликована: Янв. 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.

Язык: Английский

Процитировано

43

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

Pratiksha Bhorali,

Sabera Sultana, Sanjib Gogoi

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(4)

Опубликована: Март 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.

Язык: Английский

Процитировано

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 87(2), С. 1124 - 1132

Опубликована: Дек. 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.

Язык: Английский

Процитировано

42

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

Trayambek Nath Chaubey,

Paran J. Borpatra, Ajay Sharma

и другие.

Organic Letters, Год журнала: 2022, Номер 24(43), С. 8062 - 8066

Опубликована: Окт. 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2021, Номер 23(19), С. 7407 - 7411

Опубликована: Сен. 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.

Язык: Английский

Процитировано

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

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(26), С. 12274 - 12278

Опубликована: Янв. 1, 2023

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

Язык: Английский

Процитировано

15

Rh(iii)-Catalyzed sequential ortho-C–H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones DOI

Yaqun Dong,

Jin‐Tao Yu, Song Sun

и другие.

Chemical Communications, Год журнала: 2020, Номер 56(49), С. 6688 - 6691

Опубликована: Янв. 1, 2020

A rhodium(iii)-catalyzed ortho-C-H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in served as a chelation group. This protocol leads to efficient formation 2-hydroxy-6H-benzo[c]chromen-6-one derivatives, proceeding cleavage C(O)-S bond ylides. featured high chemo-selectivity and functional group tolerance, acted aroyl sources.

Язык: Английский

Процитировано

39

Rh(III)‐Catalyzed Diverse C—H Functionalization of Iminopyridinium Ylides DOI
Zhenzhen Dong, Pengfei Li, Xingwei Li

и другие.

Chinese Journal of Chemistry, Год журнала: 2021, Номер 39(9), С. 2489 - 2494

Опубликована: Май 9, 2021

Main observation and conclusion Divergent synthesis of useful skeletons has been realized via rhodium(III)‐catalyzed C—H activation iminopyridinium ylides coupling with various unsaturated reagents. Isocoumarins isoquinolones were obtained cleavage the C—N or N—N bond in ylidic directing group, while fluorinated alkenes delivered group intact. The reactions occurred wide substrate scopes good efficiency under redox‐neutral air‐tolerant conditions. Representative products exhibit solid‐state fluorescent property bioactivity inhibition toward human cancer cells.

Язык: Английский

Процитировано

32