Silver-Catalyzed Cascade Cyclization Reaction of Isocyanides with Sulfoxonium Ylides: Synthesis of 3-Aminofurans and 4-Aminoquinolines DOI

Yong‐Xin Liang,

Ming Yang, Bowen He

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(19), P. 7640 - 7644

Published: Sept. 15, 2020

A silver-catalyzed cascade cyclization reaction of isocyanides with sulfoxonium ylides has been developed for the first time. This provides a new and efficient method construction highly functionalized 3-aminofurans 4-aminoquinolines from readily available starting materials in single step.

Language: Английский

Recent advances in cobalt-catalysed C–H functionalizations DOI

Alessio Baccalini,

Stefania Vergura,

Pravas Dolui

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(48), P. 10119 - 10141

Published: Jan. 1, 2019

Ready availability, low cost and toxicity of cobalt salts have redirected the attention researchers away from noble metals, such as Pd, Rh, Ir, towards Co in field C-H functionalization. In this context, examples Co-catalysed functionalization exponentially grown over last few decades. This present review focuses on most recent developments C(sp2)-H C(sp3)-H functionalizations. Included is also a comprehensive overview enantioselective transformations.

Language: Английский

Citations

123
Cp*M-Catalyzed Direct Annulation with Terminal Alkynes and Their Surrogates for the Construction of Multi-Ring Systems DOI
Yuji Nishii, Masahiro Miura

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(17), P. 9747 - 9757

Published: Aug. 3, 2020

Transition-metal-catalyzed C–H activation followed by oxidative cyclization with unsaturated coupling partners has been a valuable synthetic tool for the multiring molecular scaffolds. This Perspective introduces recent progress on Cp*M-catalyzed (M = Co, Rh, and Ir) direct annulation of functionalized arenes terminal alkynes their equivalents through bond cleavage. The highlighted examples are categorized according to 10 different types reagents used in transformations. representative conditions, selected reaction scope, key mechanistic aspects briefly summarized.

Language: Английский

Citations

122
RuII-Catalyzed/NH2-Assisted Selective Alkenyl C–H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines DOI
Pu Chen, Jiang Nan, Yan Hu

et al.

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

Citations

105
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
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
Rhodium(III)-Catalyzed Regioselective C3–H Acylmethylation of [2,2′-Bipyridine]-6-carboxamides with Sulfoxonium Ylides DOI
Jia Yu,

Si Wen,

Dan Ba

et al.

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

Citations

56
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
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