Rh(III)‐Catalyzed Aldehydic C−H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides DOI
Guodong Xu,

Kenneth L. Huang,

Zhi‐Zhen Huang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(14), P. 3318 - 3323

Published: May 1, 2019

Abstract A novel aldehydic C−H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. plausible mechanism involving C( sp 2 )−H activation by catalyzed carbene insertion is also proposed. It was found that the followed dehydrative cyclization able produce flavonoids one‐pot. magnified image

Language: Английский

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

Rhodium-Catalyzed Reaction of Sulfoxonium Ylides and Anthranils toward Indoloindolones via a (4 + 1) Annulation DOI
Xiaopeng Wu, Yan Xiao, Song Sun

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(17), P. 6653 - 6657

Published: Aug. 19, 2019

A rhodium-catalyzed annulation between aroyl sulfoxonium ylides and anthranils has been developed to synthesize 10H-indolo[1,2-a]indol-10-one derivatives. This reaction started with an unpredented (4 + 1) toward N-(2-formylphenyl) indolones, proceeding the sequential ortho-amination of C–H bond in by insertion N–H carbene. Finally, Aldol condensation constructed second indole ring. procedure features formation two C–N bonds one C═C pot.

Language: Английский

Citations

87

Ruthenium(ii)-catalyzed selective C–H bond activation of imidamides and coupling with sulfoxonium ylides: an efficient approach for the synthesis of highly functional 3-ketoindoles DOI
Chenglin Wu, Jianhui Zhou, Guoxue He

et al.

Organic Chemistry Frontiers, Journal Year: 2019, Volume and Issue: 6(8), P. 1183 - 1188

Published: Jan. 1, 2019

Ruthenium-catalyzed selective C–H bond activation of imidamides and annulation sulfoxonium ylides were achieved, which afforded a series 3-ketoindole derivatives in good yields, with functional group compatibility.

Language: Английский

Citations

84

Transition Metal Promoted Cascade Heterocycle Synthesis through C−H Functionalization DOI

Alessio Baccalini,

Giuseppe Faita,

Giuseppe Zanoni

et al.

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(44), P. 9749 - 9783

Published: June 18, 2020

Sequential, domino and tandem reactions could be defined as a sequence of synthetic transformations that occur one after the other, in same reaction flask. This Review highlights recent advances at overlap two worlds: transition-metal mediated C-H activation trigger cascade reaction, for heterocycles synthesis. To shed some light on this intricate "middle-earth", focus was put mechanism rather than type metal or chronological order reaction. The aim is to separate, then highlight, true initiated by activation, compared other examples functionalization heterocycle syntheses.

Language: Английский

Citations

76

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008 DOI
Raghuram Gujjarappa, Nagaraju Vodnala, Chandi C. Malakar

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(22), P. 4896 - 4990

Published: Aug. 19, 2020

Abstract In the past decades, an enormous number of reports have been dedicated towards synthesis nitrogen containing heterocycles. This immense interest emerged owing to their wide varieties pharmacological activities. The present review focused on isoquinoline derivatives, a family N ‐heterocycles showing broad range structural diversity, biological and pharmaceutical progress synthetic strategies using versatile approaches are discussed in details. magnified image

Language: Английский

Citations

76

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

Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones DOI
Chunsheng Li, Meng Li,

Wentao Zhong

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(4), P. 872 - 875

Published: Feb. 6, 2019

The first examples of palladium-catalyzed allylic C–H oxidative allylation sulfoxonium ylides to afford the corresponding conjugated dienones with moderate good yields have been established. features this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.

Language: Английский

Citations

73