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

et al.

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 39(9), P. 2489 - 2494

Published: May 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.

Language: Английский

Sulfoxonium ylides: simple compounds with chameleonic reactivity DOI
Giorgiana Denisa Bisag, Silvia Ruggieri, Mariafrancesca Fochi

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(43), P. 8793 - 8809

Published: Jan. 1, 2020

Sulfur ylides first disclosed in 1930 started to gain more attention the 1960s, thanks mainly studies by Corey and Chaykovsky on their use for preparation of strained rings. More recently, chemistry these compounds has experienced important growth, part due similarity reactivities with diazo compounds. This short review provides an overview great assortment reactions sulfoxonium ylides, outlining a comparison between congeners: sulfonium Insertion reactions, cyclisation ring-opening are highlighted, giving particular catalytic asymmetric methodologies.

Language: Английский

Citations

117

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

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

Iridium-catalyzed B–H insertion of sulfoxonium ylides and borane adducts: a versatile platform to α-boryl carbonyls DOI
Shang‐Shi Zhang, Hui Xie, Bing Shu

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 56(3), P. 423 - 426

Published: Dec. 4, 2019

Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields most cases (51 examples; up 84%). This practical scalable reaction showed broad substrate scope, high functional-group compatibility could be applied late-stage modification structurally complex drug compounds. Further synthetic applications were also demonstrated.

Language: Английский

Citations

75

Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides DOI
Shuai Zhu, Kai Shi, Hao Zhu

et al.

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

Citations

61

Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C–H Activation/Cyclopropanation Cascade DOI
Jiang Lou, Quannan Wang, Yong‐Gui Zhou

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(22), P. 9217 - 9222

Published: Nov. 5, 2019

Rhodium(III)-catalyzed annulative coupling of sulfoxonium ylides with allenoates was achieved, forming highly functionalized cyclopropanes a quaternary carbon center by means the ylide functionality as traceless bifunctional directing group and C4 synthon via an arene C–H activation cyclopropanation cascade. The protocol features simultaneous formation three new C–C bonds in one pot excellent diastereoselectivity. resultant products could be further transformed to diverse synthetically useful compounds.

Language: Английский

Citations

60

Thioether-Directed C4-Selective C–H Acylmethylation of Indoles Using α-Carbonyl Sulfoxonium Ylides DOI

Chandrababu Naidu Kona,

Yuji Nishii, Masahiro Miura

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(12), P. 4806 - 4811

Published: June 1, 2020

Site-selective direct functionalization of an indole benzenoid core has been a great challenge due to its inherently poor reactivity. We herein demonstrate iridium-catalyzed C4-selective acylmethylation indoles using α-carbonyl sulfoxonium ylides as carbene precursors. This method exhibits high efficiency and broad functional group compatibility. The directing was easily removed or converted other functionalities after the catalysis. potential synthetic utility coupling products highlighted by constructing medium-sized polycyclic indoles.

Language: Английский

Citations

59

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

Shunsuke Ando,

Naoto Chatani

et al.

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

Citations

56

Anthranils: versatile building blocks in the construction of C–N bonds and N-heterocycles DOI Open Access
Yang Gao,

Jianhong Nie,

Yanping Huo

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(9), P. 1177 - 1196

Published: Jan. 1, 2020

This review article provides an overview of the recent progress in transformations anthranils, which have emerged as versatile building blocks assembly various C–N bonds and medicinally active heterocyclic systems.

Language: Английский

Citations

55

Ruthenium-Catalyzed Chemoselective N–H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides DOI
Xiaofeng Liu, Ying Shao, Jiangtao Sun

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(3), P. 1038 - 1043

Published: Jan. 21, 2021

A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, affording N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to achieve this unprecedented N–H rather than O–H insertion reaction is the use CpRu(PPh3)2Cl as catalyst sulfoxonium ylides alkylation reagents. Moreover, protocol also amenable 7-azaindoles by slightly varying conditions. Furthermore, sulfonium are suitable reagents, providing selectivity.

Language: Английский

Citations

50