Iridium-catalyzed arylation of sulfoxonium ylides and arylboronic acids: a straightforward preparation of α-aryl ketones DOI
Bing Shu,

Xiaotong Wang,

Zi-Xuan Shen

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(14), P. 1802 - 1808

Published: Jan. 1, 2020

A highly efficient iridium(iii)-catalyzed arylation coupling of sulfoxonium ylides with arylboronic acids to generate α-aryl ketones has been established for the first time.

Language: Английский

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 C–C/C–N Coupling of 2-Arylquinazolinones with Vinylene Carbonate: Access to Fused Quinazolinones DOI
Zhaohui Wang, He Wang, Hua Wang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(3), P. 995 - 999

Published: Jan. 27, 2021

In this work, ruthenium(II)-catalyzed C–C/C–N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range substrates excellent functional-group compatibility. transformation, the acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and plausible cycle was also proposed.

Language: Английский

Citations

70
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
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
Rh(iii)-catalyzed C–H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins DOI
Chuanliu Yin, Lianghao Li, Chuanming Yu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(5), P. 1112 - 1116

Published: Jan. 1, 2022

The direct synthesis of isocoumarin skeletons has been realized through the Rh( iii )-catalyzed [3 + 3] annulation sulfoxonium ylides and iodonium under mild conditions.

Language: Английский

Citations

33
Synthetic progress of organic thermally activated delayed fluorescence emitters via C–H activation and functionalization DOI

Fan Ni,

Yipan Huang,

Longzhen Qiu

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(11), P. 5904 - 5955

Published: Jan. 1, 2024

Thermally activated delayed fluorescence (TADF) emitters have become increasingly prominent due to their promising applications across various fields, prompting a continuous demand for developing reliable synthetic methods access them. This review aims highlight the progress made in last decade synthesizing organic TADF compounds through C-H bond activation and functionalization. The begins with brief introduction basic features design principles of emitters. It then provides an overview advantages concise development transformations constructing Subsequently, it summarizes both transition-metal-catalyzed non-transition-metal-promoted used synthesis Finally, gives outlook on further challenges potential directions this field.

Language: Английский

Citations

8
A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of N‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐a]indol‐1‐ones Derivatives DOI
Hui Xie,

Mei Zhong,

Hua‐Jie Kang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(5), P. 1436 - 1442

Published: Jan. 21, 2021

Abstract A highly efficient cascade Rh(III)‐catalyzed C−H activation/intramolecular chemodivergent cyclization reaction of N‐carbamoylindoles and sulfoxonium ylides has been successfully achieved for the first time. This synergistic process provides rapid access to functionalized dihydropyrimidoindolone tricyclic [1,3]oxazino[3,4‐ a ]indol‐1‐ones skeletons under redox neutral conditions with broad substrate scope remarkable functional‐group compatibility. Further late‐stage modification structurally complex drug molecules mechanistic studies were also accomplished. magnified image

Language: Английский

Citations

40
Synthesis of Indenone Derivatives by Rh(III)-Catalyzed C–H Functionalization of Sulfoxonium Ylides with 1,3-Diynes DOI
Sanjeev Kumar, Saiprasad Nunewar,

Tharun Kumar Sabbi

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(18), P. 3395 - 3400

Published: May 5, 2022

The transition-metal-catalyzed C-H functionalization of sulfoxonium ylides with alkynes formally participates in [4 + 2] annulations to deliver the naphthol scaffolds. In contrast, herein we disclose first Rh(III)-catalyzed activation, followed by redox-neutral [3 annulation 1,3-diynes, which delivers alkynated indenone derivatives. This protocol features a good functional group tolerance, broad substrate scope, moderate excellent yields, and mild reaction conditions. mechanism was supported through ESI-HRMS characterizing key intermediates catalytic cycle.

Language: Английский

Citations

23